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Total synthesis of balanol, part 2. Completion of the synthesis and investigation of the structure and reactivity of two key heterocyclic intermediates

✍ Scribed by David Tanner; Lars Tedenborg; Antonio Almario; Ingrid Pettersson; Ingeborg Csöregh; Nicholas M. Kelly; Pher G. Andersson; Thomas Högberg

Book ID: 104207699
Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 674 KB
Volume: 53
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(97)00167-1

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✦ Synopsis

A convergent enantioselective total synthesis of the natural product (-)-balanol (1) is described. In addition to benzophenone fragment 8, key intermediates are chiral bicyclic aziridine 3 and the corresponding epoxide 4, both of which undergo highly regio-and stereoselective nucleophilic ring-opening reactions, allowing control of the two stereogenic centres of the target molecule. The structure and reactivity of 3 and 4 have been investigated in some detail.

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