Asymmetric formal synthesis of (+)-cycloclavine

The asymmetric synthesis of Szántay's amine (+)- 2 , the pivotal precursor for direct access to (+)-cycloclavine ( 1 ), is described for the first time in eleven steps with 19.7% overall yield from the commercially available 4-bromoindole. The strategy features an asymmetric induction by Ellman...

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Bibliographic Details
Published in	Chemical communications (Cambridge, England) Vol. 53; no. 96; pp. 12902 - 12905
Main Authors	Chen, Jin-Quan, Song, Le-Le, Li, Feng-Xing, Shi, Zi-Fa, Cao, Xiao-Ping
Format	Journal Article
Language	English
Published	CAMBRIDGE Royal Soc Chemistry 30.11.2017 Royal Society of Chemistry
Subjects	amines Asymmetry catalytic activity Chemistry Chemistry, Multidisciplinary ergot alkaloids Isomerization Physical Sciences Rhodium Science & Technology stereoselective synthesis Synthesis CLAVINE ALKALOIDS ALLENYL ALCOHOLS TERT-BUTANESULFINYL IMINES LACTONES AMINES ERGOT ALKALOIDS (+/-)-CYCLOCLAVINE SELECTIVE SYNTHESIS VINYLOGOUS MANNICH REACTIONS ENANTIOSELECTIVE TOTAL-SYNTHESIS
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ISSN	1359-7345 1364-548X 1364-548X
DOI	10.1039/C7CC08044A

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Summary:	The asymmetric synthesis of Szántay's amine (+)- 2 , the pivotal precursor for direct access to (+)-cycloclavine ( 1 ), is described for the first time in eleven steps with 19.7% overall yield from the commercially available 4-bromoindole. The strategy features an asymmetric induction by Ellman's sulfinimine and rhodium-catalysed isomerization of the CC bond.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 content type line 23
ISSN:	1359-7345 1364-548X 1364-548X
DOI:	10.1039/C7CC08044A