An efficient asymmetric synthesis of grenadamide

R Green, M Cheeseman, S Duffill, A Merritt, S D Bull

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

The cyclopropane containing natural product grenadamide has been prepared in six steps using (R)-5,5-dimethyl-oxazolidin-2-one as a chiral auxiliary for asymmetric synthesis. Key synthetic steps include the use of the P-hydroxyl group of a syn-aldol product as a 'temporary' stereocentre to control the facial selectivity of a directed cyclopropanation reaction, as well as the use of phenylethylamine as a nucleophile for the direct aminolysis of an N-acyl-oxazolidin-2-one intermediate. (c) 2005 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)7931-7934
Number of pages4
JournalTetrahedron Letters
Volume46
Issue number46
DOIs
Publication statusPublished - 2005

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