Synthesis 2005(14): 2421-2425  
DOI: 10.1055/s-2005-870018
PAPER
© Georg Thieme Verlag Stuttgart · New York

An Efficient Synthesis of Carlosic Acid and Other 5-Carboxymethyltetronates from Malates

Rainer Schobert*, Carsten Jagusch
Organisch-chemisches Laboratorium der Universität Bayreuth, Gebäude NW I, 95440 Bayreuth, Germany
Fax: +49(921)552671; e-Mail: Rainer.Schobert@uni-bayreuth.de;
Further Information

Publication History

Received 16 March 2005
Publication Date:
14 July 2005 (online)

Abstract

S-Carlosic acid was prepared in six steps and 32% yield from malic acid. Ring closure was effected by a domino addition-Wittig alkenation reaction with Ph3PCCO. A variant employing resin-bound malates furnished immobilized 5-carboxymethyltetron­ates. It should be amenable to parallelization and automation.

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