We thank Dr. Yong-Xin Li for X-ray analyses. We gratefully acknowledge the Nanyang Technological University and the Singapore Ministry of Education Academic Research Fund Tier 2 (MOE2010- T2-2-067 and MOE2011-T2-1-013) for financial support.
Synthesis of 3-Oxaterpenoids and Its Application in the Total Synthesis of (±)-Moluccanic Acid Methyl Ester†
Article first published online: 17 SEP 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 42, pages 10619–10623, October 15, 2012
How to Cite
Li, B., Lai, Y.-C., Zhao, Y., Wong, Y.-H., Shen, Z.-L. and Loh, T.-P. (2012), Synthesis of 3-Oxaterpenoids and Its Application in the Total Synthesis of (±)-Moluccanic Acid Methyl Ester . Angew. Chem. Int. Ed., 51: 10619–10623. doi: 10.1002/anie.201205981
- Issue published online: 10 OCT 2012
- Article first published online: 17 SEP 2012
- Manuscript Received: 26 JUL 2012
- Nanyang Technological University
- Singapore Ministry of Education. Grant Numbers: MOE2010- T2-2-067, MOE2011-T2-1-013
- indium bromide;
- Prins reaction;
Cascades: An InBr3-catalyzed intermolecular polyene cyclization initiated by a Prins reaction provides a concise approach to 3-oxaterpenoid derivatives. The reaction is compatible with various aldehydes, ketones, and polyolefin–alcohol substrates. In addition, the total synthesis of (±)-moluccanic acid methyl ester was achieved in seven steps by using such a Prins–polyene cyclization as the key step.