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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 biand 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 triand tetracyclic products with revealing structural features.

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