Total Syntheses of (±)-Vestitol and Bolusanthin III Using a Wittig Strategy

A Luniwal, PW Erhardt

Index: Luniwal, Amarjit; Erhardt, Paul W. Synlett, 2011 , # 11 p. 1605 - 1607

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Citation Number: 3

Abstract

Scheme 1 Synthesis of racemic vestitol and bolusanthin III. Reagents and conditions: (a) BnBr, K 2 CO 3 , MeCN, reflux, 24 h, 96%; (b) Selectfluor, I 2 , CH 2 Cl 2 -MeOH (1:5), rt, 20 h, 84%; (c) BnBr, KHCO 3 , MeCN, reflux, 15 h, 85%; (d) NaBH 4 , EtOH, 0 ˚C 1 h, rt, 10 h, 58%; (e) K 2 CO 3 , Me 2 CO, reflux, 16 h, 78%; (f) (i) Ph 3 P˙HBr, MeCN, rt, 1 h; (ii) KOt-Bu, MeOH, reflux, 24 h, 70% across two steps; (g) 10% Pd/C, EtOAc, H 2 (2.4 bar), rt, 14 h, ...