Research fellow of the Japan Society for the Promotion of Science (JSPS).
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Communication
Total Synthesis of (−)-13-Oxyingenol and its Natural Derivative†
Article first published online: 5 APR 2012
DOI: 10.1002/anie.201201383
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Ohyoshi, T., Funakubo, S., Miyazawa, Y., Niida, K., Hayakawa, I. and Kigoshi, H. (2012), Total Synthesis of (−)-13-Oxyingenol and its Natural Derivative. Angew. Chem. Int. Ed., 51: 4972–4975. doi: 10.1002/anie.201201383
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This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science, and Technology (MEXT; Japan); by a grant from the Uehara Memorial Foundation, and by a grant from the Suntory Institute for Bioorganic Research (SUNBOR GRANT). We thank the Takasago International Corp. for their gift of (S)-β-hydroxy γ-butyrolactone. We would also like to thank Prof. Daisuke Uemura (Kanagawa University) for providing a sample of the 13-oxyingenol derivative and for his helpful discussion.
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Research fellow of the Japan Society for the Promotion of Science (JSPS).
Publication History
- Issue published online: 8 MAY 2012
- Article first published online: 5 APR 2012
- Manuscript Received: 20 FEB 2012
Funded by
- Ministry of Education, Culture, Sports, Science, and Technology (MEXT; Japan)
Keywords:
- 13-oxyingenol;
- inside–outside framework;
- metathesis;
- sigmatropic rearrangement;
- terpenoids
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.