Synthesis of Alcohols from m-Fluorophenylsulfones and Dialkylboranes: Application to the C14-C35 Building Block of E7389

Lei Liu (1) , James A. Henderson , Akihiko Yamamoto , Paul Brémond (2) , Yoshito Kishi

1 Nanyang Cigarette Factory of China Tobacco Henan Industrial Corporation
2 ICR - Institut de Chimie Radicalaire

The reaction of m-fluorophenylsulfone anions with dialkylboranes, followed by alkaline hydroperoxide oxidation, yields alcohols in high yields. Optimization of the process, scope and limitation, and application to the synthesis of one of the C14-C35 building blocks of E7389, a right half analogue of halichondrin B, are reported.

Domains: Chemical Sciences

Lei Liu, James A. Henderson, Akihiko Yamamoto, Paul Brémond, Yoshito Kishi. Synthesis of Alcohols from m-Fluorophenylsulfones and Dialkylboranes: Application to the C14-C35 Building Block of E7389. Organic Letters, 2012, 14 (9), pp.2262--2265. ⟨10.1021/ol300672q⟩. ⟨hal-01460413⟩