Formal synthesis of Cladospolide C & epi-Cladospolide C using R-(+)-γ-valerolactone as a chiral synthon

Tetrahedron(2019)

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摘要
The formal synthesis of Cladospolide-C and its analog is achieved by using enantiopure (R)-γ–valerolactone 10. The significant points of this synthesis are the stereoselective dihydroxylation of α, β-unsaturated ester 16 using Sharpless protocol, Wittig olefination of γ –valerolactol 6 with triphenylphosphonium iodide salt 7, one pot selective oxidation of 22 and subsequent C2-homologation with good E/Z ratio.
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关键词
Cladospolide,Gamma valerolactone,Wittig reaction,Yamaguchi lactonization
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