Asymmetric Synthesis of the Seco-Acids of (R,R)-Pyrenophorin and (R)-Patulolide A Monitored by a Chiral Sulfoxide Group

Guy Solladié; Christine Gerber

doi:10.1055/s-1992-21377

Synlett 1992; 1992(5): 449-450
DOI: 10.1055/s-1992-21377

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Asymmetric Synthesis of the Seco-Acids of (R,R)-Pyrenophorin and (R)-Patulolide A Monitored by a Chiral Sulfoxide Group

Guy Solladié^* , Christine Gerber

^*Ecole Européene des Hautes Etudes des Industries Chimiques, Laboratoire de Stéréochimie, Associé au CNRS, 1 Rue Blaise Pascal, F-67008 Strasbourg, France

Abstract

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The title compounds [(R)-7-hydroxy-4-oxo-2-octenoic acid (1) and 4,11-di-O-protected ethyl (4RS, 11R)-4,11-dihydroxy-2-dodecenoate (11)] were prepared in optically pure form by an asymmetric synthesis monitored by a chiral sulfoxide group. In the case of the patulolide A precursor the 4-oxo-2-butenoic moiety was prepared by using an allylic sulfoxide-sulfenate rearrangement.

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