Research fellow of the Japan Society for the Promotion of Science (JSPS).
Total Synthesis of (−)-13-Oxyingenol and its Natural Derivative†
Article first published online: 5 APR 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 20, pages 4972–4975, May 14, 2012
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
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.
- Issue published online: 8 MAY 2012
- Article first published online: 5 APR 2012
- Manuscript Received: 20 FEB 2012
- Ministry of Education, Culture, Sports, Science, and Technology (MEXT; Japan)
- inside–outside framework;
- sigmatropic rearrangement;
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.