Total synthesis of norzoanthamine.

Abstract

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).

• Authors: Masaaki Miyashita, Minoru Sasaki, Izumi Hattori, Mio Sakai, Keiji Tanino
• Journal: Science (New York, N.Y.) (Science) Vol. 305 Issue 5683 Pg. 495-9 (Jul 23 2004) ISSN: 1095-9203 [Electronic] United States
• PMID: 15205476 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Alkaloids
• Azepines
• Heterocyclic Compounds, 4 or More Rings
• Quinolines
• norzoanthamine

Topics

• Alkaloids
• Azepines (chemical synthesis, chemistry, pharmacology)
• Heterocyclic Compounds, 4 or More Rings
• Molecular Conformation
• Molecular Structure
• Oxidation-Reduction
• Quinolines (chemical synthesis, chemistry, pharmacology)
• Stereoisomerism