ASYMMETRIC-SYNTHESIS OF 1-HYDROXYINDOLIZIDINES, BIOSYNTHETIC PRECURSORS TO THE TOXIC INDOLIZIDINE ALKALOIDS SLAFRAMINE AND SWAINSONINE

An enantioselective synthesis of 1-hydroxyindolizidines (1 and 2) from racemic N-benzyloxycarbonyl-3-hydroxy-4-pentenylamine (3) by folllowing the Sharpless kinetic resolution, intramolecular amidomercuration, and radical Michael addition as key steps is described.

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 1; no. 11; pp. 763 - 764
Main Authors TAKAHATA, H, BANBA, Y, MOMOSE, T
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.01.1990
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
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Summary:An enantioselective synthesis of 1-hydroxyindolizidines (1 and 2) from racemic N-benzyloxycarbonyl-3-hydroxy-4-pentenylamine (3) by folllowing the Sharpless kinetic resolution, intramolecular amidomercuration, and radical Michael addition as key steps is described.
ISSN:0957-4166
DOI:10.1016/S0957-4166(00)80439-5