Download PDF
Synlett 1992; 1992(5): 449-450
DOI: 10.1055/s-1992-21377
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
08 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

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.