Journal
TETRAHEDRON LETTERS
Volume 54, Issue 14, Pages 1893-1896Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2013.01.121
Keywords
(R)-(+)-Crispine A; Pictet-Spengler reaction; N-Sulfinyl amines; Remote stereocontrol; N-desulfinylation
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Funding
- DGAPA-UNAM [Proyecto IN206910]
- Spanish Government [CTQ-2012-35957]
- CAM [AVANCAT CS2009/PPQ-1634]
- DGAPA-UNAM
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We report the highly stereoselective synthesis of (R)-(+)-crispine A from the (R)-N-sulfinyl amine 1 by using a one-pot process involving the Pictet-Spengler reaction with 4-chlorobutanal, removal of the sulfinyl group by protonolysis of the N-S bond and in situ cyclization, with a 55% overall yield. (C) 2013 Elsevier Ltd. All rights reserved.
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