Synthesis 2004(15): 2493-2498  
DOI: 10.1055/s-2004-831240
PAPER
© Georg Thieme Verlag Stuttgart · New York

First Total Synthesis of (±)-Prelunularin

Horacio Comas, Enrique Pandolfi*
Departamento de Química Orgánica, Facultad de Química, Universidad de la República., Av. Gral. Flores 2124, CC 1157, Montevideo, Uruguay
Fax: +598(2)9241906; e-Mail: epandolf@fq.edu.uy;
Further Information

Publication History

Received 20 May 2004
Publication Date:
22 September 2004 (online)

Abstract

The first total synthesis of (±)-prelunularin is described employing an intramolecular aldol addition/sulfinate elimination tandem reaction. Investigations on the mechanism of the one-pot cyclization reaction using time-dependent NMR spectroscopy suggested that the sulfinate elimination took place before the intramolecular ring-closing aldol addition.