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  • Title: Enantioselective synthesis of the C1-C11 fragment of bafilomycin A1 using non-Wittig and desymmetrization strategies.
    Author: Poupon JC, Demont E, Prunet J, Férézou JP.
    Journal: J Org Chem; 2003 Jun 13; 68(12):4700-7. PubMed ID: 12790573.
    Abstract:
    The synthesis of the C1-C11 fragment 33 of bafilomycin A(1) was achieved. Intermediate ketone 16 was prepared in six steps from 4-oxopimelate 13. Desymmetrization of this ketone using Koga's chiral base followed by TMSCl quench furnished silyl enol ether 17 with excellent enantioselectivity. Further elaboration led to C5-C11 aldehyde 24, which was coupled with sulfone 3 to give lactone 25 in very good yield. The subsequent reductive elimination created the E-trisubstituted C4-C5 olefin with a 13:1 selectivity. The E C2-C3 double bond was then installed by methanol elimination, and compound 33 was obtained after a few functional group manipulations and a Negishi methyl zirconation.
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