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Synthesis 2012; 44(9): 1365-1372
DOI: 10.1055/s-0031-1290771
DOI: 10.1055/s-0031-1290771
paper
First Stereoselective Total Synthesis of Cryptomoscatone D2 and Syntheses of (5R,7S)-Kurzilactone and (+)-Cryptofolione by an Asymmetric Acetate Aldol Approach
Further Information
Publication History
Received: 29 December 2011
Accepted after revision: 22 February 2012
Publication Date:
05 April 2012 (online)
Abstract
An efficient concise stereoselective total synthesis of cryptomoscatone D2 and syntheses of (5R,7S)-kurzilactone and (+)-cryptofolione, based on an asymmetric acetate aldol reaction starting from trans-cinnamaldehyde, are described. The other key reactions are a Horner–Wadsworth–Emmons reaction, a Brown’s asymmetric allylation and a ring-closing metathesis.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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Procedures for the syn aldol reaction were adapted from:
For the generation of 1,3-diol units with anti-geometry, see: