Dedicated to Professor Elias J. Corey on the occasion of his 65th birthday
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Review
The Total Synthesis of Brevetoxin B: A Twelve-Year Odyssey in Organic Synthesis†
Article first published online: 22 DEC 2003
DOI: 10.1002/anie.199605881
Copyright © 1996 by VCH Verlagsgesellschaft mbH, Germany
Issue
Angewandte Chemie International Edition in English
Volume 35, Issue 6, pages 588–607, April 1, 1996
Additional Information
How to Cite
Nicolaou, K. C. (1996), The Total Synthesis of Brevetoxin B: A Twelve-Year Odyssey in Organic Synthesis. Angewandte Chemie International Edition in English, 35: 588–607. doi: 10.1002/anie.199605881
- †
Publication History
- Issue published online: 22 DEC 2003
- Article first published online: 22 DEC 2003
- Manuscript Received: 30 MAR 1995
- Abstract
- References
- Cited By
Keywords:
- brevetoxin B;
- natural products;
- total syntheses
- Brevetoxins;
- Natural products;
- Total synthesis
Graphical Abstract
What is the connection between the total synthesis of brevetoxin and the 1994 Soccer World Cup? Apparently irrelevant factors have extensive ramifications for natural product syntheses. The marine biotoxin brevetoxin B, which is responsible for mass poisoning of humans and marine life during “red tides”, was the target of an intense research program in the Nicolaou group. Their perseverance paid off with a wealth of new reactions as dividends. In this “story behind the story” the author describes both the successes and failures along the way.
Abstract
The total synthesis of brevetoxin B has been achieved recently after a long search for a suitable pathway. This twelve-year odyssey† in synthetic organic chemistry was marked by several strategic and tactical routes, and resulted in numerous new synthetic methods. This article is a behind-thescenes account of the total synthesis of brevetoxin B, from its origins at the University of Pennsylvania to its completion at the University of California, San Diego, and The Scripps Research Institute, La Jolla, California.