Diastereoselective Aldol Reactions of β-Silyloxy Ethyl Ketones. Application to the Total Synthesis of Bafilomycin A1

DOI: 10.1016/S0040-4039(00)91817-3

Source and publish data:

Tetrahedron Letters p. 6871 - 6874 (1993)

Update date:2022-08-31

Topics:

Authors:

Evans, David A.

Calter, Michael A.

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Article abstract of DOI:10.1016/S0040-4039(00)91817-3

Studies directed toward the C₁₇-C₁₈ aldol bond construction in the macrolide antibiotic bafilomycin A₁ are described.The effect of the β-substituent in the aldol reactions of α-unsubstituted enolates is documented for various model compounds.The stereoselectivity of this process is critically dependent on the C₂₁ and C₂₃ oxygen protecting groups.Application of this methodology to the synthesis of bafilomycin A₁ is reported.

Full text of DOI:10.1016/S0040-4039(00)91817-3

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