☆ 4.8 Article

Enantioselective Organocatalytic Michael/Aldol Sequence: Anticancer Natural Product (+)-trans-Dihydrolycoricidine

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

期刊

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

卷 53, 期 32, 页码 8450-8454

出版社

WILEY-V C H VERLAG GMBH

DOI: 10.1002/anie.201403065

关键词

alkaloids; asymmetric synthesis; natural products; organocatalysis; total synthesis

类别

Chemistry, Multidisciplinary

资金

NSERC
CONACyT

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Protocol

Reagent

摘要

A total synthesis of the anticancer natural product (+)-trans-dihydrolycoricidine is reported from alpha-azidoacetone and cinnamaldehyde precursors. Key elements include an asymmetric organocatalytic sequence proceeding by a regio-specific secondary-amine-catalyzed syn Michael addition followed by an intramolecular aldol reaction. The sequence results in the formation of an advanced intermediate, containing three stereogenic centers, in one step which and was converted into the title compound in eight steps.

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