Taxol semisynthesis: a highly enantio-and diastereoselective synthesis of the side chain and a new method for ester formation at C-13 using thioesters

…, M Carcano, M Donghi, N Mongelli…

Index: Gennari, Cesare; Carcano, Michela; Donghi, Monica; Mongelli, Nicola; Vanotti, Ermes; Vulpetti, Anna Journal of Organic Chemistry, 1997 , vol. 62, # 14 p. 4746 - 4755

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Citation Number: 41

Abstract

A very simple, new, and straightforward approach to the Paclitaxel (Taxol) and Docetaxel (Taxotere) side chains has been developed using the imine addition reaction of thioester- derived boron enolates bearing chiral ligands. The addition reaction was studied extensively, using a combination of different thioesters (ROCH2COSPh, ROCH2COS t-Bu), oxygen protecting groups (R= Bn, TBDMS, COPh, EE, TMS), chiral boron ligands [derived ...