A concise approach for the synthesis of bitungolides: total syntheses of (?)-bitungolide B & E?

Organic & Biomolecular Chemistry Pub Date: 2014-03-25 DOI: 10.1039/C4OB00250D

Abstract

The first total synthesis of (?)-bitungolide B and a second-generation total synthesis of (?)-bitungolide E are described. The cornerstone of the approach comprises a convergent and flexible route involving Brown crotylation, highly diastereoselective substrate controlled Paterson anti-aldol reaction, hydroxyl-directed 1,3-syn/anti reduction, Barton–McCombie deoxygenation and RCM reactions. Via this route, a common intermediate 13 is readily accessible for the synthesis of the family of bitungolides A–E and franklinolides A–C.

Graphical abstract: A concise approach for the synthesis of bitungolides: total syntheses of (?)-bitungolide B & E
Recommended Literature