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.
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