A Concise and Efficient Stereoselective Synthesis of the C1-C11 Fragment of Macrolactin A

Abstract A stereoselective synthesis of the C1-C11 fragment of macrolactin A, using original approaches for the introduction of the Z,E-diene stereochemistry and the C-7 stereogenic center, is reported. The adopted strategy has allowed us to build up the fragment by the assembly of three key interme...

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Bibliographic Details
Published in:Synlett 2006-09, Vol.2006 (15), p.2427-2430
Main Authors: Bonini, Carlo, Chiummiento, Lucia, Videtta, Valeria, Colobert, Françoise, Solladié, Guy
Format: Article
Language:English
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Summary:Abstract A stereoselective synthesis of the C1-C11 fragment of macrolactin A, using original approaches for the introduction of the Z,E-diene stereochemistry and the C-7 stereogenic center, is reported. The adopted strategy has allowed us to build up the fragment by the assembly of three key intermediates via cross-metathesis, Still-Gennari, and Wittig olefinations. Opening of the commercially available chiral benzyl glycidol epoxide to the corresponding ­homoallylic alcohol introduced the C-7 chiral center. A cross-meta­thesis reaction was used to create the C5-C4 E double bond. The Still-Gennari reaction introduced the 2Z,4E-diene moiety and ­finally the Wittig reaction with a propargylic triphenylphosphorane introduced directly the 1,3-enyne unit in a highly efficient stereo­selective fashion.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2006-950424