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• W2952455259 startingPage "4700" @default.
• W2952455259 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." @default.
• W2952455259 created "2019-06-27" @default.
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• W2952455259 date "2003-05-16" @default.
• W2952455259 modified "2023-10-03" @default.
• W2952455259 title "Enantioselective Synthesis of the C1−C11 Fragment of Bafilomycin A₁Using Non-Wittig and Desymmetrization Strategies" @default.
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• W2952455259 doi "https://doi.org/10.1021/jo034018e" @default.
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