This research was supported in part by a Grant-in-Aid for Scientific Research (B; KAKENHI No. 18390010) from the Japan Society for the Promotion of Science.
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Communication
Synthetic Study of (−)-Norzoanthamine: Construction of the ABC Ring Moiety†
Article first published online: 26 NOV 2008
DOI: 10.1002/anie.200804544
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Murata, Y., Yamashita, D., Kitahara, K., Minasako, Y., Nakazaki, A. and Kobayashi, S. (2009), Synthetic Study of (−)-Norzoanthamine: Construction of the ABC Ring Moiety. Angew. Chem. Int. Ed., 48: 1400–1403. doi: 10.1002/anie.200804544
- †
Publication History
- Issue published online: 30 JAN 2009
- Article first published online: 26 NOV 2008
- Manuscript Received: 16 SEP 2008
Funded by
- Japan Society for the Promotion of Science. Grant Number: 18390010
Keywords:
- diastereoselectivity;
- Diels–Alder reaction;
- Michael addition;
- natural products;
- total synthesis
Abstract
Throw your hat in the ring: A highly diastereoselective synthesis of the ABC rings of (−)-norzoanthamine has been achieved starting from the (−)-Hajos–Parrish ketone (see scheme). Three asymmetric quaternary carbon centers on the C ring were constructed by a 1,4-addition, and an intramolecular Diels–Alder reaction provided a trans-decalin scaffold on the AB rings.