Diastereoselective Synthesis of a Simplified Core of Rishirilide B.
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.
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.
Lupe
L
Mejorado
Thomas R R
TR
Pettus