Synthesis 2006(19): 3209-3214  
DOI: 10.1055/s-2006-950188
PAPER
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Synthesis of a Simplified Core of Rishirilide B

Lupe Mejorado, Thomas R. R. Pettus*
Department of Chemistry and Biochemistry, University of California at Santa Barbara, Santa Barbara, CA 93106-9510, USA
Fax: +1(805)6375651; e-Mail: pettus@chem.ucsb.edu;
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Publikationsverlauf

Received 21 April 2006
Publikationsdatum:
15. August 2006 (online)

Abstract

A route enabling the synthesis of the stereo-triad of rishirilide B (1) from 2-hydroxy-3-methylnaphthalene-1,4-dione, is reported. Key transformations include the regioselective 1,2-Grignard addition to a tautomeric mixture of o- and p-quinones, regioselective carbamoylation of a tautomeric mixture, and a synopsis of the methods explored to convert various terminal vinyl ethers into the corresponding carboxylic acid by cleavage.