Enantioselective synthesis of the C1-C11 fragment of bafilomycin A1 using non-wittig and desymmetrization strategies

JC Poupon, E Demont, J Prunet…

文献索引：Poupon, Jean-Christophe; Demont, Emmanuel; Prunet, Joelle; Ferezou, Jean-Pierre Journal of Organic Chemistry, 2003 , vol. 68, # 12 p. 4700 - 4707

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被引用次数: 21

摘要

The synthesis of the C1-C11 fragment 33 of bafilomycin A1 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 ...