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.
Mejorado
Lupe
L
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.
Pettus
Thomas R R
TR