Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 19, Pages 8078-8081Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja302765m
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Funding
- National Natural Science Foundation of China [2117223]
- Ministry of Human Resources and Social Security of China
- State Key Laboratory of Bioorganic and Natural Products Chemistry
- Chinese Academy of Sciences
- National Science Foundation [CHE-0603217]
- Universita degli Studi di Milano
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A divergent strategy for the total syntheses of the indole terpenoid anominine (1) and its natural congener tubingensin A (2) has been developed. The common intermediate 11 bearing all of the required stereogenic centers for both natural products was first assembled by employing a Ueno-Stork radical cyclization and a Sc(OTf)(3)-mediated Mukaiyama aldol reaction to form the key C-C bonds in a stereocontrolled manner. The route to anominine features a radical deoxygenation followed by an efficient side-chain installation, while the path to tubingensin A exploits a CuOTf-promoted 6 pi-electrocyclization/aromatization sequence to forge the central region of the pentacyclic scaffold.
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