Journal
ORGANIC LETTERS
Volume 15, Issue 17, Pages 4402-4405Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol4019425
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Funding
- NSFC [21102045, 21272076]
- Shanghai Pujiang Program [11PJ1402800]
- RFDP of Higher Education of China [20110076120022]
- program for professor of special appointment (Eastern Scholar) at Shanghai institutions of higher learning
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The first total synthesis of cyanthiwigins A, C, H and concise synthesis of cyanthiwigin G was achieved from a common intermediate. A modified formal [4 + 2] cycloaddition was developed to construct the key cis-hydrindanone (A-B). Stereospecific 1,4-addition, alkylation, and ring-closing metathesis were used to build the tricarbocyclic ring system (A-B-C). Various site-selective oxidations were applied to create the desired oxidation states of the different cyanthiwigins.
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