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Synfacts 2009(8): 0830-0830  
DOI: 10.1055/s-0029-1217581
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (-)-Norzoanthamine

Contributor(s): Philip Kocienski, Arndt W. Schmidt
Y. Murata, D. Yamashita, K. Kitahara, Y. Minasako, A. Nakazaki, N. Hikage, K.-i. Takao, S. Kobayashi*
Tokyo University of Science, Chiba and Daiichi-Sankyo Co., Ltd., Kanagawa, Japan
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Publication History

Publication Date:
23 July 2009 (online)

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Significance

The Zoanthus alkaloid (-)-norzo­anthamine shows promising anti-osteoporotic activity. The complex ring system, including an unstable bisaminal motif, poses a synthetic challenge. Herein a new synthetic route starting from the easily accessible Hajos-Parrish ketone (A) is reported which utilizes an intramolecular ­Diels-Alder reaction to construct the trans-decalin AB system.