Total Synthesis of (-)-Decarbamoyloxysaxitoxin

A facile and general synthetic strategy for saxitoxin derivatives has been developed, as exemplified by the efficient synthesis of (−)‐decarbamoyloxysaxitoxin ((−)‐doSTX), the putative enantiomer of the natural product, in 17 steps and in 10 % overall yield. The synthesis features a diastereoselecti...

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Published in	Angewandte Chemie (International ed.) Vol. 46; no. 45; pp. 8625 - 8628
Main Authors	Iwamoto, Osamu, Koshino, Hiroyuki, Hashizume, Daisuke, Nagasawa, Kazuo
Format	Journal Article
Language	English
Published	Weinheim Wiley-VCH Verlag 01.01.2007 WILEY-VCH Verlag WILEY‐VCH Verlag Wiley
Subjects	Chemistry Chemistry, Multidisciplinary Cycloaddition Derivatives Enantiomers guanidine Marine Toxins - chemical synthesis Marine Toxins - chemistry Molecular Conformation Molecular Structure Natural products Oxidation Physical Sciences Saxitoxin - analogs & derivatives Saxitoxin - chemical synthesis Saxitoxin - chemistry Science & Technology sodium channels Strategy Synthesis total synthesis SAXIPHILIN oxidation BULLFROG TOXINS SAXITOXIN-BINDING PROTEIN SODIUM-CHANNEL guanidine natural products sodium channels TRANSFERRIN PURIFICATION SHELLFISH total synthesis ENANTIOSELECTIVE TOTAL-SYNTHESIS RANA-CATESBEIANA
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ISSN	1433-7851 1521-3773 1521-3773
DOI	10.1002/anie.200703326

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Summary:	A facile and general synthetic strategy for saxitoxin derivatives has been developed, as exemplified by the efficient synthesis of (−)‐decarbamoyloxysaxitoxin ((−)‐doSTX), the putative enantiomer of the natural product, in 17 steps and in 10 % overall yield. The synthesis features a diastereoselective 1,3‐dipolar cycloaddition and a direct oxidation with o‐iodoxybenzoic acid (IBX; see scheme, Cbz=benzyloxycarbonyl).
Bibliography:	http://dx.doi.org/10.1002/anie.200703326 We thank Prof. Oshima (Tohoku University) for kindly providing us with copies of the spectra of natural doSTX (3). We also thank Dr. Kei-ichi Noguchi (TUAT) for the X-ray structure analysis of 23. This work was supported by a Grant-in-Aid for Scientific Research on Priority Areas 17035025 from The Ministry of Education, Culture, Sports, Science, and Technology (MEXT). ark:/67375/WNG-735FC0DM-K Ministry of Education, Culture, Sports, Science, and Technology (MEXT) ArticleID:ANIE200703326 istex:8192829D5FA3BE68B5237071BFDD4E84C669D94C 23 This work was supported by a Grant‐in‐Aid for Scientific Research on Priority Areas 17035025 from The Ministry of Education, Culture, Sports, Science, and Technology (MEXT). 3 We thank Prof. Oshima (Tohoku University) for kindly providing us with copies of the spectra of natural doSTX We also thank Dr. Kei‐ichi Noguchi (TUAT) for the X‐ray structure analysis of ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1433-7851 1521-3773 1521-3773
DOI:	10.1002/anie.200703326