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Dr. Takayuki Ohyoshi, Shota Funakubo, Yamato Miyazawa, Keisuke Niida, Dr. Ichiro Hayakawa and Prof. Dr. Hideo Kigoshi Total Synthesis of (−)-13-Oxyingenol and its Natural Derivative Angewandte Chemie International Edition 51

Version of Record online: 5 APR 2012 | DOI: 10.1002/anie.201201383

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Ring functionalization: The total synthesis of a natural derivative of (−)-13-oxyingenol, a potent anti-HIV diterpenoid, is reported. The key steps in this synthesis include a ring-closing olefin metathesis and a Mislow–Evans-type [2,3]-sigmatropic rearrangement. This synthesis provides access to (−)-13-oxyingenol and its natural derivative in 21 steps from a synthetic intermediate previously prepared by Kigoshi and co-workers.

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