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. 2005 Apr;33(2):116-33.
doi: 10.1016/j.bioorg.2004.11.002. Epub 2004 Dec 15.

Total synthesis of 12,13-desoxyepothilone B (Epothilone D)

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Total synthesis of 12,13-desoxyepothilone B (Epothilone D)

Robert L Broadrup et al. Bioorg Chem. 2005 Apr.

Abstract

A highly convergent total synthesis of 12,13-desoxyepothilone B (4, Epothilone D) is described involving the coupling of vinyl iodide (5) and olefin (6). Key steps in the synthesis are the introduction of chirality at C15 via highly enantioselective lipase-mediated enzymatic resolution, diastereoselective alkylation at C8, highly diastereoselective Evans aldol reaction to establish C6-C7, and Mukaiyama aldol reaction to introduce chiral center C3. Palladium catalyzed Suzuki coupling of (5) and (6) provided the methyl ester (27), which was converted to 12,13-desoxyepothilone B (4).

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