Diastereoselective formal total synthesis of (+/-)-triptolide via a novel cationic cyclization of 2-alkenyl-1,3-dithiolane.

Sylvie Goncalves, Paul Hellier, Marc Nicolas, Alain Wagner, Rachid Baati

Index: Chem. Commun. (Camb.) 46(31) , 5778-80, (2010)

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Abstract

A concise and diastereoselective formal total synthesis of triptolide, a natural product with a wide range of biological properties, is described. The key reaction is an unprecedented 6-endo-Trig cationic cyclization of a 2-alkenyl-1,3-dithiolane precursor induced by TMSOTf as Lewis acid.