Affiliation:
1. Department of Chemistry, 1102 Natural Sciences II, University of California
Abstract
Two synthesis designs for the diterpenoid crotogoudin are discussed, and efforts to achieve each are described. First, a Cope rearrangement/intramolecular Diels–Alder cascade reaction was investigated. Second, a bioinspired sequence of cationic bicyclization and A-ring oxidative fragmentation set-up for a lactonization induced by a phenolic oxidation, ultimately providing a tricyclic intermediate that required only installation of the bridging ring of the salient bicyclo[2.2.2]octane system. This last endeavor was fraught with difficulty, but did lead to the development of conditions for cyclization of related keto-alkenes via manganese(III)-based radical chemistry.
Funder
National Science Foundation
Cited by
7 articles.
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