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Synthesis 2010(15): 2643-2651
DOI: 10.1055/s-0029-1218825
DOI: 10.1055/s-0029-1218825
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkSynthesis of the C1-C14 Fragment of Sarcoglaucol-16-one via Z-Selective Ando-Type Horner-Wadsworth-Emmons Olefination
Further Information
Received
26 March 2010
Publication Date:
18 June 2010 (online)
Publication History
Publication Date:
18 June 2010 (online)
Abstract
A synthetic strategy involving a Z-selective Horner-Wadsworth-Emmons olefination was developed for the preparation of the sarcoglaucolone precursor methyl (2Z,6E)-8-(methoxymethoxy)-6-methyl-2-[(3E)-4-methyl-5-oxopent-3-enyl]-9-[(trimethylsilyl)methyl]deca-2,6,9-trienoate. The target compound was isolated in a E/Z ratio of 17:83
Key words
Ando-type reaction - olefination - cembranolide - natural product - macrocycles
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