期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 140, 期 48, 页码 16704-16710出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b09685
关键词
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资金
- ETH Zurich
- Swiss National Science Foundation [205320_169135/1]
The first synthesis of (-)-mitrephorone A is disclosed along with discussion and study of synthetic strategies. The natural product includes a highly congested hexacyclic ent-trachylobane diterpenoid framework featuring a rare, embedded oxetane. The synthetic analysis presented dissects a number of approaches for the synthesis of the central oxetane, including carbonyl-olefin photocycloadditions, Prins-type cyclizations, and oxidative ring closures. In the successful route, three [4 + 2] cycloadditions enable rapid construction of all carbocycles. A novel late-stage oxidative cyclization of a hydroxy diosphenol with Kosers reagent furnishes the pivotal oxetane moiety.
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