New approach to the stereoselective synthesis of polyhydroxy compounds

ORGN 449

Hojae Choi, Bruno D. Chapsal, and Iwao Ojima. Department of Chemistry, State University of New York at Stony Brook, Stony Brook, NY 11794-3400
Developing new and efficient processes to synthesize polyhydroxy containing compounds are of great interest because this moiety is a key structural component of various powerful antibiotics and antifungal agents. A new approach to the stereoselective synthesis of polyhydroxy compounds has been studied, which includes the Rh-catalyzed intramolecular silylformylation of v-siloxyalkyne 1 as a key step. Subsequent diastereoselective hydrogenation, nucleophilic addition to aldehyde and the cleavage of Si-C bond by Tamao oxidation affords triol 3.