A concise synthesis of sex pheromone of mediterranean fruit fly, Ceratitis capitata via lithiated carbanion derived from enephosphoramide

✍ Scribed by Tomasz Krzysztof Olszewski; Claude Grison

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 286 KB
• Volume: 21
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.20588

✦ Synopsis

Abstract

A novel and versatile synthetic approach to the preparation of (E)‐non‐6‐en‐1‐ol, a sex pheromone of the Mediterranean fruit fly, Ceratitis capitata, is presented. This pheromone can be viewed as potential active component for lures designed to control and eradication of Mediterranean fruit fly. The described protocol is a six‐step reaction sequence producing the desired compound with 28% overall yield from commercially available and inexpensive starting material and total E stereoselectivity of the double bond present in final structure. The key to the success of the presented strategy is application of lithiated α‐allylphosphoramido carbanions and their reaction with halogenated acetals. © 2010 Wiley Periodicals, Inc. 21:139–147, 2010; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20588