Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Synthetic Strategies Toward Polyoxocyclic Natural Compounds
Total Synthesis of Hemibrevetoxin B
Fuminori SATO
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1995 Volume 53 Issue 4 Pages 284-297

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Abstract

Brevetoxins are powerful neurotoxins produced by dinoflagellate strain Gymnodinium berve Davis, isolated from the Florida “red tide” dinoflagellate. Their unique structure presents an opportunistic and formidable synthetic problem, particularly with regard to the construction of its medium-sized ring systems. This would almost certainly require new synthetic technology and a carefully designed strategy before yielding to total synthesis. This review deals with some new, practical and efficient synthetic technologies for the construction and chemical manipulation of medium-sized cyclic ether developed in K K.C. Nicolaou's laboratories.
First total synthesis of hemibrevetoxin B (3) performed by these technologies is also delineated.

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© The Society of Syhthetic Organic Chemistry, Japan
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