Redox Refunctionalization of Steroid Spiroketals. Structure Correction of Ritterazine M

Autor: Lee, S., LaCour, T. G., Lantrip, D., Fuchs, P. L.
Zdroj: Organic Letters; February 2002, Vol. 4 Issue: 3 p313-316, 4p
Abstrakt: The structure of the North spiroketal moiety of ritterazine M has been corrected from 1a to 1b. This was accomplished by comparison of published spectra of the natural product with five synthetic spiroketal−alcohols. Synthesis of these models was efficiently accomplished by reductive cleavage of the spiroketal and Sharpless asymmetric dihydroxylation of an isopentyl, methyl 1,1-disubstituted olefin, followed by Suarez iodine[III] oxidative spirocyclization of monoprotected 1°,3° 1,2 diols.
Databáze: Supplemental Index