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Published Online June 17, 2004
Science DOI: 10.1126/science.1098851

Reports

Submitted on April 6, 2004
Accepted on June 2, 2004

Total Synthesis of Norzoanthamine

Masaaki Miyashita 1*, Minoru Sasaki 1, Izumi Hattori 1, Mio Sakai 1, Keiji Tanino 1

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

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

Norzoanthamine, 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 39 steps with an overall yield of 3.5%.




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Science. ISSN 0036-8075 (print), 1095-9203 (online)