Conversion of tetracyclic triterpenes to steroids

Publisher Website
Google Scholar
Abstract
An alternative procedure for converting the typical 3-hydroxy-4,4-dimethyl-substituted triterpene A-ring to a steroidal 3-oxo-4-ene system has been outlined. Application of the new method to 3β-hydroxy-5α-lanostane (1) was used for illustration. Key reaction steps involved Baeyer-Villiger oxidation of ketone 3 to lactone 4 and the latter to carboxylic acid 5 employing Jones' reagent. Proceeding via enol–lactone (6) and diketone (7) led to 3-oxo-14α-methyl-cholest-4-ene (8). The first example of an oxa-14α-methyl-steroid was also reported.

This publication has 0 references indexed in Scilit: