BIOORGANIC CHEMISTRY - STEROLS AND ACYCLIC TERPENE TERMINAL EPOXIDES

Investigations into the bioorganic chemistry of sterol synthesis have led to various advances in both the organic and biological provinces. Along organic lines, there have been developed: (i) a general method for the highly selective terminal oxidation of acyclic terpenes, and (ii) stereoselective cyclizations of terpene terminal epoxides to 3-hydroxylated bi- and tricyclic terpenoids of the natural product type. In the biochemical realm, application of the above chemistry has led to (i) the identification of squalene 2,3-oxide as a genuine intermediate in the conversion of squalene to lanosterol; (ii) a fuller theoretical understanding of the cyclization process, including the recognition of alternate biochemical cyclization pathways; and (iii) the discovery that structurally modified squalene 2,3-oxides are enzymically converted to tri- and tetracyclic products with revealing structural features. © 1968, American Chemical Society. All rights reserved.