Synthetic studies on bafilomycin A1: stereoselective synthesis of the enantiopure C1-C11 fragment |
| |
Authors: | Emmanuelle Qué ron |
| |
Affiliation: | Unité Mixte CNRS-AVENTIS Pharma (UMR 26) 102, Route de Noisy, 93235 Romainville, France |
| |
Abstract: | The synthesis of the enantiopure C1-C11 fragment of bafilomycin A1 has been achieved with a 4% overall yield over 18 steps from (R)-(+)-citronellol. Key steps involve Sharpless asymmetric epoxidation, Miyashita reaction of a γ,δ-epoxymethacrylate with trimethylaluminum in the presence of water, bis-OTMS selective Swern oxidations, Corey-Fuchs alkyne formation, Negishi's carbometalation, and stereoselective formation of the C2-C3 trisubstituted bond of the conjugated diene by a Wittig-type olefination of the α,β-unsaturated C3-C11 aldehyde with the ylide derived from the readily available phosphonium salt [Cl−, Ph3P+CH(OMe)COOMe]. |
| |
Keywords: | Epoxides Aluminium and compounds Alkynes Zirconium and compounds Silyl ether selective oxidation Wittig reactions |
本文献已被 ScienceDirect 等数据库收录! |
|