A model study of epothilone synthesis: An alternative synthetic approach to the C1-C7 fragment

Abstract

In this model study an alternative synthetic approach to the C1–C7 fragment of epothilones was investigated. Starting from 4,4-dimethylcyclopentenone, a 7 step reaction sequence afforded the key intermediate 7 in 27% overall yield. Surprisingly, the attempted deprotection of latent functionalities in 7 failed, indicating the incompatibility of the ethoxyethyl protective group with the reaction conditions employed.

Keywords

• epothilones
• epoxides
• enol ethers
• alkylations
• lewis acids.