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. We thank Prof. Dr. Keiji Tanino (The Hokkaido University) for helpful suggestions.
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Communication
Total Synthesis of (−)-Norzoanthamine†
Article first published online: 3 DEC 2008
DOI: 10.1002/anie.200804546
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Yamashita, D., Murata, Y., Hikage, N., Takao, K.-i., Nakazaki, A. and Kobayashi, S. (2009), Total Synthesis of (−)-Norzoanthamine. Angew. Chem. Int. Ed., 48: 1404–1406. doi: 10.1002/anie.200804546
- †
Publication History
- Issue published online: 30 JAN 2009
- Article first published online: 3 DEC 2008
- Manuscript Received: 16 SEP 2008
Funded by
- Japan Society for the Promotion of Science. Grant Number: 18390010
Keywords:
- alkaloids;
- cleavage reactions;
- Horner–Emmons reaction;
- natural products;
- total synthesis
Abstract
No bones about it: (−)-Norzoanthamine, a promising candidate for an anti-osteoporotic drug, was the target of a total synthesis (see scheme). The final bisaminal formation with AcOH/H2O gave the DEFG ring, while the cyclization precursor was prepared by installing the remaining bisaminal unit after oxidative cleavage of the cyclopentanol moiety.