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Originally published in Science Express on 17 June 2004
Science 23 July 2004:
Vol. 305. no. 5683, pp. 495 - 499
DOI: 10.1126/science.1098851
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Reports

Total Synthesis of Norzoanthamine

Masaaki Miyashita,* Minoru Sasaki, Izumi Hattori, Mio Sakai, Keiji Tanino

Norzoanthamine, an alkaloid isolated from Zoanthus sp., can suppress the loss of bone weight and strength in ovariectomized mice. Norzoanthamine derivatives can also strongly inhibit the growth of P-388 murine leukemia cell lines and human platelet aggregation. However, norzoanthamine's densely functionalized complex stereostructure and scarce availability from natural sources have proved a synthetic challenge. We report the stereoselective total synthesis of norzoanthamine in 41 steps, with an overall yield of 3.5% (an average of 92% yield each step).

Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan.

* To whom correspondence should be addressed. E-mail: miyasita{at}sci.hokudai.ac.jp

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