Asymmetric synthesis of H1 receptor antagonist (R,R)-clemastine
The first asymmetric synthesis of ( R , R )-clemastine ( 1 ) has been accomplished by the coupling of ( R )-tertiary alcohol 2 and ( R )-chloroethylpyrrolidine 3 via O -alkylation. ( R )-Tertiary alcohol 2 was synthesized by stereoselective alkylation of chiral α-benzyloxy ketone with Grignard reage...
Saved in:
| Published in | Archives of pharmacal research Vol. 38; no. 12; pp. 2131 - 2136 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
Seoul
Pharmaceutical Society of Korea
01.12.2015
대한약학회 |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0253-6269 1976-3786 1976-3786 |
| DOI | 10.1007/s12272-015-0641-4 |
Cover
| Abstract | The first asymmetric synthesis of (
R
,
R
)-clemastine (
1
) has been accomplished by the coupling of (
R
)-tertiary alcohol
2
and (
R
)-chloroethylpyrrolidine
3
via
O
-alkylation. (
R
)-Tertiary alcohol
2
was synthesized by stereoselective alkylation of chiral α-benzyloxy ketone with Grignard reagent via chelation-controlled 1,4-asymmetric induction. In the reaction, chiral benzyl group acts as a chiral auxiliary as well as a protecting group. (
R
)-Chloroethylpyrrolidine
3
was prepared by asymmetric transformation starting with
l
-homoserine lactone, in which racemization-minimized
N
-allylation and ring-closing metathesis were involved as key steps. |
|---|---|
| AbstractList | The first asymmetric synthesis of (R,R)-clemastine (1) has been accomplished by the coupling of (R)-tertiary alcohol 2 and (R)-chloroethylpyrrolidine 3 via O-alkylation. (R)-Tertiary alcohol 2 was synthesized by stereoselective alkylation of chiral α-benzyloxy ketone with Grignard reagent via chelation-controlled 1,4-asymmetric induction. In the reaction, chiral benzyl group acts as a chiral auxiliary as well as a protecting group. (R)-Chloroethylpyrrolidine 3 was prepared by asymmetric transformation starting with L-homoserine lactone, in which racemization-minimized N-allylation and ring-closing metathesis were involved as key steps. The first asymmetric synthesis of (R,R)-clemastine (1) has been accomplished by the coupling of (R)-tertiary alcohol 2 and (R)-chloroethylpyrrolidine 3 via O-alkylation. (R)-Tertiary alcohol 2 was synthesized by stereoselective alkylation of chiral α-benzyloxy ketone with Grignard reagent via chelation-controlled 1,4-asymmetric induction. In the reaction, chiral benzyl group acts as a chiral auxiliary as well as a protecting group. (R)-Chloroethylpyrrolidine 3 was prepared by asymmetric transformation starting with L-homoserine lactone, in which racemization-minimized N-allylation and ring-closing metathesis were involved as key steps.The first asymmetric synthesis of (R,R)-clemastine (1) has been accomplished by the coupling of (R)-tertiary alcohol 2 and (R)-chloroethylpyrrolidine 3 via O-alkylation. (R)-Tertiary alcohol 2 was synthesized by stereoselective alkylation of chiral α-benzyloxy ketone with Grignard reagent via chelation-controlled 1,4-asymmetric induction. In the reaction, chiral benzyl group acts as a chiral auxiliary as well as a protecting group. (R)-Chloroethylpyrrolidine 3 was prepared by asymmetric transformation starting with L-homoserine lactone, in which racemization-minimized N-allylation and ring-closing metathesis were involved as key steps. The first asymmetric synthesis of (R,R)-clemastine (1) has been accomplished by the coupling of (R)-tertiary alcohol 2 and (R)-chloroethylpyrrolidine 3 via O-alkylation. (R)-Tertiary alcohol 2 was synthesized by stereoselective alkylation of chiral a-benzyloxy ketone with Grignard reagent via chelation-controlled 1,4-asymmetric induction. In the reaction, chiral benzyl group acts as a chiral auxiliary as well as a protecting group. (R)-Chloroethylpyrrolidine 3 was prepared by asymmetric transformation starting with L-homoserine lactone, in which racemization-minimized N-allylation and ring-closing metathesis were involved as key steps. KCI Citation Count: 5 The first asymmetric synthesis of ( R , R )-clemastine ( 1 ) has been accomplished by the coupling of ( R )-tertiary alcohol 2 and ( R )-chloroethylpyrrolidine 3 via O -alkylation. ( R )-Tertiary alcohol 2 was synthesized by stereoselective alkylation of chiral α-benzyloxy ketone with Grignard reagent via chelation-controlled 1,4-asymmetric induction. In the reaction, chiral benzyl group acts as a chiral auxiliary as well as a protecting group. ( R )-Chloroethylpyrrolidine 3 was prepared by asymmetric transformation starting with l -homoserine lactone, in which racemization-minimized N -allylation and ring-closing metathesis were involved as key steps. |
| Author | Kim, Tae-Hyun Jung, Jung Wha Kim, Hee-Doo Lee, Sun Young |
| Author_xml | – sequence: 1 givenname: Sun Young surname: Lee fullname: Lee, Sun Young organization: College of Pharmacy, Sookmyung Women’s University – sequence: 2 givenname: Jung Wha surname: Jung fullname: Jung, Jung Wha organization: College of Pharmacy, Sookmyung Women’s University – sequence: 3 givenname: Tae-Hyun surname: Kim fullname: Kim, Tae-Hyun organization: College of Pharmacy, Sookmyung Women’s University – sequence: 4 givenname: Hee-Doo surname: Kim fullname: Kim, Hee-Doo email: hdkim@sm.ac.kr organization: College of Pharmacy, Sookmyung Women’s University |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/26219510$$D View this record in MEDLINE/PubMed https://www.kci.go.kr/kciportal/ci/sereArticleSearch/ciSereArtiView.kci?sereArticleSearchBean.artiId=ART002056579$$DAccess content in National Research Foundation of Korea (NRF) |
| BookMark | eNqFkUFvFCEUgImpsdvVH-DFzLFNOsqDAYaT2TTaNmlisqlnQtk3K-0MrMAe9t_LOtWDh8rlXb6PF_jOyEmIAQl5D_QjUKo-ZWBMsZaCaKnsoO1ekQVoJVuuenlCFpQJ3kom9Sk5y_mRUi6FEG_IKZMMtAC6IJ9X-TBNWJJ3TT6E8gOzz00cmhtoEjrclZgaG4rdxuBzac7Xl-uL1o042Vx8wLfk9WDHjO-e55J8__rl_uqmvft2fXu1umtdB1DaTnBEx0Hy3lElBHP6QfENOMu4AznYATdDp52TA0dQVmsUTAPbMK7VoBlfkov53pAG8-S8idb_nttonpJZre9vDQCXfd20JOczu0vx5x5zMZPPDsfRBoz7bBg9nvp-9V-0In0PfadkRT88o_uHCTdml_xk08H8-csKwAy4FHNOOPxFgJpjLzP3MrWXOfYyXXXUP47zxRYfQ0nWjy-abDZz3RK2mMxj3KdQG7wg_QLof6Xo |
| CitedBy_id | crossref_primary_10_1007_s10562_018_2406_4 crossref_primary_10_1016_j_ccr_2016_08_007 crossref_primary_10_3390_catal12070730 crossref_primary_10_3390_ijms252011158 crossref_primary_10_1002_ejoc_201800751 crossref_primary_10_1007_s00210_025_03978_3 crossref_primary_10_1039_D4MD01004C |
| Cites_doi | 10.1055/s-0034-1380461 10.1080/00397919008053128 10.1002/chem.200501397 10.1007/BF02977320 10.1021/ol100627c 10.1038/nature07592 10.1016/j.tetasy.2011.11.005 10.1002/hlca.19760590721 10.1039/c39850001636 10.1016/S0040-4039(00)00031-9 10.1021/jo961189t 10.1016/j.tetasy.2008.06.007 10.1002/ejoc.201402935 10.1055/s-0033-1340163 10.1016/j.tet.2011.09.073 |
| ContentType | Journal Article |
| Copyright | The Pharmaceutical Society of Korea 2015 |
| Copyright_xml | – notice: The Pharmaceutical Society of Korea 2015 |
| DBID | AAYXX CITATION CGR CUY CVF ECM EIF NPM 7X8 7S9 L.6 ACYCR |
| DOI | 10.1007/s12272-015-0641-4 |
| DatabaseName | CrossRef Medline MEDLINE MEDLINE (Ovid) MEDLINE MEDLINE PubMed MEDLINE - Academic AGRICOLA AGRICOLA - Academic Korean Citation Index |
| DatabaseTitle | CrossRef MEDLINE Medline Complete MEDLINE with Full Text PubMed MEDLINE (Ovid) MEDLINE - Academic AGRICOLA AGRICOLA - Academic |
| DatabaseTitleList | AGRICOLA MEDLINE - Academic MEDLINE |
| Database_xml | – sequence: 1 dbid: NPM name: PubMed url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed sourceTypes: Index Database – sequence: 2 dbid: EIF name: MEDLINE url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/medline/basic-search sourceTypes: Index Database |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Medicine Pharmacy, Therapeutics, & Pharmacology |
| EISSN | 1976-3786 |
| EndPage | 2136 |
| ExternalDocumentID | oai_kci_go_kr_ARTI_1136845 26219510 10_1007_s12272_015_0641_4 |
| Genre | Research Support, Non-U.S. Gov't Journal Article |
| GrantInformation_xml | – fundername: Sookmyung Women’s University Research Grants 2012 |
| GroupedDBID | --- -53 -56 -5G -BR -EM -Y2 -~C .86 .UV .VR 06C 06D 0R~ 0VY 1N0 2.D 203 23N 29~ 2J2 2JN 2JY 2KG 2KM 2LR 2VQ 2WC 2~H 30V 3SX 4.4 406 408 40D 40E 53G 5GY 5VS 67N 67Z 6J9 6NX 8TC 8UJ 95- 95. 95~ 96X 9ZL AAAVM AABHQ AACDK AAHBH AAHNG AAIAL AAJBT AAJKR AANXM AANZL AARHV AARTL AASML AATNV AATVU AAUYE AAWCG AAYIU AAYQN AAYTO AAYZH ABAKF ABDZT ABECU ABFTV ABHQN ABJNI ABJOX ABKCH ABMNI ABMQK ABNWP ABPLI ABQBU ABQSL ABSXP ABTEG ABTKH ABTMW ABWNU ABXPI ACAOD ACBXY ACDTI ACGFO ACGFS ACHSB ACHXU ACKNC ACMDZ ACMLO ACOKC ACOMO ACPIV ACREN ACSNA ACUDM ACZOJ ADHHG ADHIR ADINQ ADKNI ADKPE ADRFC ADTPH ADURQ ADYFF ADYOE ADZKW AEBTG AEFQL AEGAL AEGNC AEJHL AEJRE AEKMD AEMSY AENEX AEOHA AEPYU AESKC AETLH AEVLU AEXYK AFBBN AFGCZ AFLOW AFQWF AFWTZ AFYQB AFZKB AGAYW AGDGC AGGDS AGJBK AGMZJ AGQEE AGQMX AGRTI AGWIL AGWZB AGYKE AHAVH AHBYD AHKAY AHSBF AHYZX AIAKS AIGIU AIIXL AILAN AITGF AJBLW AJRNO AJZVZ AKMHD ALMA_UNASSIGNED_HOLDINGS ALWAN AMKLP AMTXH AMXSW AMYLF AMYQR AOCGG ARMRJ ASPBG AVWKF AXYYD AZFZN B-. BA0 BBWZM BDATZ BGNMA C1A CAG COF CS3 CSCUP DDRTE DNIVK DPUIP EBLON EBS EIOEI EJD EMOBN ESBYG F5P FEDTE FERAY FFXSO FIGPU FINBP FNLPD FRRFC FSGXE FWDCC G-Y G-Z GGCAI GGRSB GJIRD GNWQR GQ6 GQ7 GRRUI H13 HF~ HG6 HMJXF HRMNR HVGLF HZ~ IJ- IKXTQ IWAJR IXC IXD I~X I~Z J-C J0Z JBSCW JZLTJ KOV KPH KVFHK LLZTM M4Y MA- MZR N2Q N9A NDZJH NF0 NPVJJ NQJWS NU0 O9- O93 O9G O9I O9J OVD P19 P2P PF0 PT4 PT5 QOK QOR QOS R89 R9I RHV RNI RNS ROL RPX RSV RZK S16 S1Z S26 S27 S28 S3A S3B SAP SBL SCLPG SDE SDH SHX SISQX SJN SJYHP SNE SNPRN SNX SOHCF SOJ SPISZ SRMVM SSLCW SSXJD STPWE SZ9 SZN T13 T16 TEORI TSG TSK TUC U2A U9L UG4 UOJIU UTJUX UZXMN VC2 VFIZW W48 WK6 WK8 YLTOR Z45 Z7U Z7V Z7W Z83 Z87 Z8O Z8P Z8Q Z91 ZMTXR ZOVNA ZZE ~A9 AAPKM AAYXX ABBRH ABDBE ABFSG ABRTQ ACSTC ADHKG AEZWR AFDZB AFHIU AFOHR AGQPQ AHPBZ AHWEU AIXLP ATHPR AYFIA CITATION CGR CUY CVF ECM EIF NPM 7X8 7S9 L.6 AABYN AAFGU AAKSU AAPBV AAYFA ABFGW ABKAS ACBMV ACBRV ACBYP ACIGE ACIPQ ACTTH ACVWB ACWMK ACYCR ADMDM ADOXG AEEQQ AEFTE AESTI AEVTX AFAFS AFNRJ AGGBP AGKHE AIMYW AJDOV AKQUC UNUBA Z7X |
| ID | FETCH-LOGICAL-c411t-453eec31638c07552c9b73d1ca23c16fafedf49cc6f3e17a99e52912d2397f923 |
| IEDL.DBID | AGYKE |
| ISSN | 0253-6269 1976-3786 |
| IngestDate | Tue Nov 21 21:30:00 EST 2023 Wed Oct 01 14:31:27 EDT 2025 Wed Oct 01 14:30:35 EDT 2025 Wed Feb 19 01:57:57 EST 2025 Wed Oct 01 04:24:53 EDT 2025 Thu Apr 24 22:56:26 EDT 2025 Fri Feb 21 02:37:03 EST 2025 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 12 |
| Keywords | Asymmetric synthesis Asymmetric transformation ( H Clemastine , receptor antagonist (R,R)-Clemastine H1 receptor antagonist |
| Language | English |
| LinkModel | DirectLink |
| MergedId | FETCHMERGED-LOGICAL-c411t-453eec31638c07552c9b73d1ca23c16fafedf49cc6f3e17a99e52912d2397f923 |
| Notes | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 G704-000010.2015.38.12.013 |
| PMID | 26219510 |
| PQID | 1738818476 |
| PQPubID | 23479 |
| PageCount | 6 |
| ParticipantIDs | nrf_kci_oai_kci_go_kr_ARTI_1136845 proquest_miscellaneous_2000009517 proquest_miscellaneous_1738818476 pubmed_primary_26219510 crossref_primary_10_1007_s12272_015_0641_4 crossref_citationtrail_10_1007_s12272_015_0641_4 springer_journals_10_1007_s12272_015_0641_4 |
| ProviderPackageCode | CITATION AAYXX |
| PublicationCentury | 2000 |
| PublicationDate | 20151200 2015-12-00 2015-Dec 20151201 2015-12 |
| PublicationDateYYYYMMDD | 2015-12-01 |
| PublicationDate_xml | – month: 12 year: 2015 text: 20151200 |
| PublicationDecade | 2010 |
| PublicationPlace | Seoul |
| PublicationPlace_xml | – name: Seoul – name: Korea (South) |
| PublicationTitle | Archives of pharmacal research |
| PublicationTitleAbbrev | Arch. Pharm. Res |
| PublicationTitleAlternate | Arch Pharm Res |
| PublicationYear | 2015 |
| Publisher | Pharmaceutical Society of Korea 대한약학회 |
| Publisher_xml | – name: Pharmaceutical Society of Korea – name: 대한약학회 |
| References | Jung, Ho, Kim (CR7) 2000; 41 Shimizu, Uetsu, Takahashi, Ito (CR14) 2015; 26 Fernández-Mateos, Marciá, Yus (CR3) 2014; 29 Sato, Kobayashi, Takahashi, Chiba, Takeda, Kusakabe (CR13) 1985; 22 Fournier, Brown, Farnaby, Miyatake-Ondozabal, Clayden (CR5) 2010; 12 Nelson, Williams, Thomas (CR11) 2002 CR16 Ebnöther, Weber (CR2) 1976; 59 Kim, Chang, Kim (CR9) 2011; 22 Chang, Kim, Kim (CR1) 2008; 19 Han, Wang, Wang (CR6) 2011; 67 Kim, Kim, Yang, Jung, Jeong, Kim (CR10) 2014; 25 Stymiest, Bagutski, French, Aggarwal (CR15) 2008; 456 Vanhessche, Sharpless (CR17) 1996; 61 Nikiforov, Stanchev, Milenkov, Dimitrov (CR12) 1990; 20 Jung, Kim (CR8) 2007; 30 Forrat, Prieto, Ramón, Yus (CR4) 2006; 12 T Nikiforov (641_CR12) 1990; 20 WL Nelson (641_CR11) 2002 JE Jung (641_CR7) 2000; 41 E Fernández-Mateos (641_CR3) 2014; 29 K Shimizu (641_CR14) 2015; 26 TH Kim (641_CR10) 2014; 25 M Chang (641_CR1) 2008; 19 A Ebnöther (641_CR2) 1976; 59 JW Jung (641_CR8) 2007; 30 F Sato (641_CR13) 1985; 22 JL Stymiest (641_CR15) 2008; 456 SJ Kim (641_CR9) 2011; 22 641_CR16 KPM Vanhessche (641_CR17) 1996; 61 AM Fournier (641_CR5) 2010; 12 P Han (641_CR6) 2011; 67 VJ Forrat (641_CR4) 2006; 12 |
| References_xml | – volume: 26 start-page: 1238 year: 2015 end-page: 1242 ident: CR14 article-title: Zn(salen)-catalyzed enantioselective phenyl transfer to aldehydes and ketones with organozinc reagent publication-title: Synlett doi: 10.1055/s-0034-1380461 – volume: 20 start-page: 1977 year: 1990 end-page: 1981 ident: CR12 article-title: A route to optically active benzyl ester of (1-methyl-2-pyrrolidinyl)acetic acid, an intermediate in the synthesis of clemastine publication-title: Synthetic Communications doi: 10.1080/00397919008053128 – volume: 12 start-page: 4431 year: 2006 end-page: 4445 ident: CR4 article-title: -1-Sufonylamino-2-isoborneolsulfonylaminocyclohexane derivatives: Excellent chiral ligands for catalytic enantioselective addition of organozinc reagents to ketones publication-title: Chemistry-A European Journal doi: 10.1002/chem.200501397 – volume: 30 start-page: 1521 year: 2007 end-page: 1525 ident: CR8 article-title: Stereoselective synthesis of (–)-hydroxyclemastine as a versatile intermediate for the H receptor antagonist clemastine publication-title: Archives of Pharmacal Research doi: 10.1007/BF02977320 – volume: 12 start-page: 2222 year: 2010 end-page: 2225 ident: CR5 article-title: Synthesis of (–)-( , )-clemastine by invertive N → C aryl migration in lithiated carbamate publication-title: Organic Letters doi: 10.1021/ol100627c – volume: 456 start-page: 778 year: 2008 end-page: 783 ident: CR15 article-title: Enantiodivergent conversion of chiral secondary alcohols into tertiary alcohols publication-title: Nature doi: 10.1038/nature07592 – ident: CR16 – volume: 22 start-page: 1901 year: 2011 end-page: 1905 ident: CR9 article-title: Asymmetric transformation of -homoserine lactone to an optically active 2-substituted pyrrolidine for clemastine publication-title: Tetrahedron Asymmetry doi: 10.1016/j.tetasy.2011.11.005 – volume: 59 start-page: 2462 year: 1976 end-page: 2468 ident: CR2 article-title: Synthesis and absolute configuration of clemastine and its isomers publication-title: Helvetica Chimica Acta doi: 10.1002/hlca.19760590721 – volume: 22 start-page: 1636 year: 1985 end-page: 1638 ident: CR13 article-title: Synthesis of the rarely obtained -adducts in the reaction of organocopper compounds with 2,3- -isopropylideneglyceraldehyde. Preparation of optically active epoxy alcohols publication-title: Journal of the Chemical Society, Chemical Communications doi: 10.1039/c39850001636 – volume: 41 start-page: 1793 year: 2000 end-page: 1796 ident: CR7 article-title: Bidentate chelation-controlled asymmetric synthesis of α-hydroxy esters based on the glycolate enolate alkylation publication-title: Tetrahedron Letters doi: 10.1016/S0040-4039(00)00031-9 – start-page: 794 year: 2002 end-page: 818 ident: CR11 article-title: Antihistamines and related antiallergic and antiulcer agents publication-title: Foye’s principles of medicinal chemistry – volume: 61 start-page: 7978 year: 1996 end-page: 7979 ident: CR17 article-title: Ligand-dependent reversal of facial selectivity in asymmetric dihydroxylation publication-title: Journal of Organic Chemistry doi: 10.1021/jo961189t – volume: 19 start-page: 1503 year: 2008 end-page: 1507 ident: CR1 article-title: Stereoselective synthesis of (+)-flutriafol publication-title: Tetrahedron Asymmetry doi: 10.1016/j.tetasy.2008.06.007 – volume: 29 start-page: 6519 year: 2014 end-page: 6526 ident: CR3 article-title: Catalytic enantioselective addition of aryl Grignard reagents to ketones publication-title: European Journal of Organic Chemistry doi: 10.1002/ejoc.201402935 – volume: 25 start-page: 251 year: 2014 end-page: 254 ident: CR10 article-title: A chiral benzyl group as a chiral auxiliary and protecting group for the synthesis of optically active 1,2-diols and (+)-frontalin publication-title: Synlett doi: 10.1055/s-0033-1340163 – volume: 67 start-page: 8873 year: 2011 end-page: 8878 ident: CR6 article-title: Electronic polarizability-based stereochemical model for Sharpless AD reactions publication-title: Tetrahedron doi: 10.1016/j.tet.2011.09.073 – volume: 20 start-page: 1977 year: 1990 ident: 641_CR12 publication-title: Synthetic Communications doi: 10.1080/00397919008053128 – volume: 67 start-page: 8873 year: 2011 ident: 641_CR6 publication-title: Tetrahedron doi: 10.1016/j.tet.2011.09.073 – volume: 41 start-page: 1793 year: 2000 ident: 641_CR7 publication-title: Tetrahedron Letters doi: 10.1016/S0040-4039(00)00031-9 – volume: 59 start-page: 2462 year: 1976 ident: 641_CR2 publication-title: Helvetica Chimica Acta doi: 10.1002/hlca.19760590721 – volume: 61 start-page: 7978 year: 1996 ident: 641_CR17 publication-title: Journal of Organic Chemistry doi: 10.1021/jo961189t – volume: 19 start-page: 1503 year: 2008 ident: 641_CR1 publication-title: Tetrahedron Asymmetry doi: 10.1016/j.tetasy.2008.06.007 – volume: 456 start-page: 778 year: 2008 ident: 641_CR15 publication-title: Nature doi: 10.1038/nature07592 – volume: 29 start-page: 6519 year: 2014 ident: 641_CR3 publication-title: European Journal of Organic Chemistry doi: 10.1002/ejoc.201402935 – volume: 22 start-page: 1901 year: 2011 ident: 641_CR9 publication-title: Tetrahedron Asymmetry doi: 10.1016/j.tetasy.2011.11.005 – start-page: 794 volume-title: Foye’s principles of medicinal chemistry year: 2002 ident: 641_CR11 – volume: 12 start-page: 4431 year: 2006 ident: 641_CR4 publication-title: Chemistry-A European Journal doi: 10.1002/chem.200501397 – volume: 25 start-page: 251 year: 2014 ident: 641_CR10 publication-title: Synlett doi: 10.1055/s-0033-1340163 – volume: 22 start-page: 1636 year: 1985 ident: 641_CR13 publication-title: Journal of the Chemical Society, Chemical Communications doi: 10.1039/c39850001636 – volume: 26 start-page: 1238 year: 2015 ident: 641_CR14 publication-title: Synlett doi: 10.1055/s-0034-1380461 – volume: 12 start-page: 2222 year: 2010 ident: 641_CR5 publication-title: Organic Letters doi: 10.1021/ol100627c – volume: 30 start-page: 1521 year: 2007 ident: 641_CR8 publication-title: Archives of Pharmacal Research doi: 10.1007/BF02977320 – ident: 641_CR16 |
| SSID | ssj0036555 |
| Score | 2.138022 |
| Snippet | The first asymmetric synthesis of (
R
,
R
)-clemastine (
1
) has been accomplished by the coupling of (
R
)-tertiary alcohol
2
and (
R
)-chloroethylpyrrolidine... The first asymmetric synthesis of (R,R)-clemastine (1) has been accomplished by the coupling of (R)-tertiary alcohol 2 and (R)-chloroethylpyrrolidine 3 via... |
| SourceID | nrf proquest pubmed crossref springer |
| SourceType | Open Website Aggregation Database Index Database Enrichment Source Publisher |
| StartPage | 2131 |
| SubjectTerms | alcohols alkylation antagonists Chemistry, Pharmaceutical - methods Clemastine - chemical synthesis Histamine H1 Antagonists - chemical synthesis Medicine Pharmacology/Toxicology Pharmacy Receptors, Histamine H1 - chemistry Research Article Stereoisomerism 약학 |
| Title | Asymmetric synthesis of H1 receptor antagonist (R,R)-clemastine |
| URI | https://link.springer.com/article/10.1007/s12272-015-0641-4 https://www.ncbi.nlm.nih.gov/pubmed/26219510 https://www.proquest.com/docview/1738818476 https://www.proquest.com/docview/2000009517 https://www.kci.go.kr/kciportal/ci/sereArticleSearch/ciSereArtiView.kci?sereArticleSearchBean.artiId=ART002056579 |
| Volume | 38 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| ispartofPNX | Archives of Pharmacal Research, 2015, 38(12), , pp.2131-2136 |
| journalDatabaseRights | – providerCode: PRVLSH databaseName: SpringerLink Journals customDbUrl: mediaType: online eissn: 1976-3786 dateEnd: 99991231 omitProxy: false ssIdentifier: ssj0036555 issn: 0253-6269 databaseCode: AFBBN dateStart: 19970201 isFulltext: true providerName: Library Specific Holdings – providerCode: PRVAVX databaseName: SpringerLINK - Czech Republic Consortium customDbUrl: eissn: 1976-3786 dateEnd: 99991231 omitProxy: false ssIdentifier: ssj0036555 issn: 0253-6269 databaseCode: AGYKE dateStart: 19970101 isFulltext: true titleUrlDefault: http://link.springer.com providerName: Springer Nature – providerCode: PRVAVX databaseName: SpringerLink Journals (ICM) customDbUrl: eissn: 1976-3786 dateEnd: 99991231 omitProxy: true ssIdentifier: ssj0036555 issn: 0253-6269 databaseCode: U2A dateStart: 19970101 isFulltext: true titleUrlDefault: http://www.springerlink.com/journals/ providerName: Springer Nature |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwlV3da9swED-WFMZe9tF9uduCNkbZR1wsybLjp5GOZtlGSykJtE9ClqVS0tglTh6yv34nfzRsawd9ysvFlnWnu99xp98BvKeJ4jYSymd6kPqhCJTvphT6JkhToQ1LM-YuJx8eReNp-ONUnDb3uMu2270tSVaeenPZjbHYtREIH8MoJj4d2BIuP-nC1vDb2c-D1gHzSFTDTjGacx_xetIWM296yB_hqJMv7E1I858qaRV8Ro9g0i677jmZ7a2W6Z7-9Rej4x2_6zE8bMAoGdbW8wTumXwb7h825fZt2D2uia3XfTLZ3NMq-2SXHG8or9dP4cuwXM_nbjiXJuU6R1BZXpSksGRMCbpUc4WZPUEdqvPCMfWSDyf9k48-vnOu0MXk5hlMRweTr2O_Gc3g65DSJSqVG6O5A3MaQYdgOkljnlGtGNc0ssqazIaJ1pHlhsYqSYxgCWUZQ_xjEVQ-h25e5OYlkChgCt1KjNCLh2GmFVcBChurA50qyj0IWg1J3fCWu_EZl3LDuOx2UOIOSreDMvTg0_VfrmrSjv8Jv0O1y5m-kI5q2_2eF3K2kJhQfJdu5M0gFB68ba1C4vlzRRWVm2JVShrzAYKeMI5ul2FVKoZYNvbgRW1S1-tiEcYMdIwefG7NQzZupLx90Tt3kn4FD5izr6oL5zV0l4uVeYNYapn28OyM9vePes0Z6kFnyoa_AaLVEyQ |
| linkProvider | Springer Nature |
| linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwlV1Lb9NAEB7RVAIuPAoU81wQqoBmK-_DrxOKUEtKm6qqUqmcVuv1uqpC7CpODuHXM-tHI6BF6smXsb3eGc98q5n5BuADS7TIw0BTbuKUysDX1E0ppNZP08BYnmbcNSePjsLhqfx-Fpy1fdxVV-3epSRrT71qduM8cmUEAcUwigefNViXLI5lD9YH334c7HYOWIRBPewUo7mgiNeTLpl53UP-CEdrxSy_Dmn-kyWtg8_eQxh3y25qTiY7i3m6Y379xeh4y-96BA9aMEoGjfU8hju22IC7ozbdvgFbxw2x9bJPxqs-rapPtsjxivJ6-QS-DKrldOqGcxlSLQsEldVFRcqcDBlBl2ov8WRPUIf6vHRMveTjSf_kE8V3TjW6mMI-hdO93fHXIW1HM1AjGZujUoW1RjgwZxB0BNwkaSQyZjQXhoW5zm2Wy8SYMBeWRTpJbMATxjOO-CdHUPkMekVZ2OdAQp9rdCsRQi8hZWa00D4K29z4JtVMeOB3GlKm5S134zN-qhXjsttBhTuo3A4q6cHnq1suG9KO_wm_R7WriblQjmrbXc9LNZkpPFDsKzfyJpaBB-86q1D4_7mkii5suagUi0SMoEdG4c0yvD6KIZaNPNhsTOpqXTzEmIGO0YPtzjxU60aqmxf94lbSb-HecDw6VIf7Rwcv4T53tlZX5LyC3ny2sK8RV83TN-1_9BuowROw |
| linkToPdf | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwlV3da9RAEB9sheKLaP2Kn6tIUXtLs1_J5UkO9biqLUfpQd-WzWa3lHrJcbk-3H_vbD56iK3gU14myTKzO_MbZuc3AO9ZZoRPlKHcDnMqVWxomFJIXZznyjqeFzw0Jx8dJ5OZ_H6mzro5p3V_270vSbY9DYGlqVwdLAp_sGl84zwNVwoUxZCKSdAW3JUYqkP2NeOj3hWLRDVjTzGuC4rIPevLmjd94o_AtFUu_U2Y8696aROGxg_gfocfyag1-EO448pd2DnqKuS7sDdtuajXA3K6aa2qB2SPTDcs1etH8HlUr-fzME_LknpdIg6sL2pSeTJhBL2gW2AyTlDt5rwK5Lrkw8ng5CPFf84NeoXSPYbZ-NvplwntpilQKxlboR2Ec1YE_GURJyhuszwVBbOGC8sSb7wrvMysTbxwLDVZ5hTPGC84QhaPOPAJbJdV6Z4BSWJu0BOkiJaElIU1wsQo7LyNbW6YiCDuValtRzUeJl780huS5KB9jdrXQftaRvDp-pVFy7PxL-F3aB99aS90YMcOz_NKXy415gCHOkypGUoVwdvefBqPTKiDmNJVV7VmqRgiTpFpcrsMb7InhJ9pBE9b21-viyfo5tGXRbDfbwbdnfz69kU__y_pN7Az_TrWPw-Pf7yAezxs0-YOzUvYXi2v3CtEQqv8dbPbfwN0ZPsj |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Asymmetric+synthesis+of+H1+receptor+antagonist+%28R%2CR%29-clemastine&rft.jtitle=Archives+of+pharmacal+research&rft.au=Lee%2C+Sun+Young&rft.au=Jung%2C+Jung+Wha&rft.au=Kim%2C+Tae-Hyun&rft.au=Kim%2C+Hee-Doo&rft.date=2015-12-01&rft.issn=0253-6269&rft.volume=38&rft.issue=12&rft.spage=2131&rft_id=info:doi/10.1007%2Fs12272-015-0641-4&rft_id=info%3Apmid%2F26219510&rft.externalDocID=26219510 |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0253-6269&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0253-6269&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0253-6269&client=summon |