Lithiated anions derived from (alkenyl)pentamethyl phosphoric triamides: Useful synthons for the stereoselective synthesis of 9-oxo- and 10-hydroxy-2(E)-decenoic acids, important components of queen substance and royal jelly of honeybee Apis mellifera
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- 作者：Tomasz K. Olszewski ; Catherine Bomont ; Philippe Coutrot ; Claude Grison
- 关键词：Homoenolate anion ; Enephosphoramide carbanion ; Carbonyl protecting group ; Chemical messengers ; Natural compounds
- 刊名：Journal of Organometallic Chemistry
- 出版年：2010
- 出版时间：1 October 2010
- 年：2010
- 卷：695
- 期：21
- 页码：2354-2358
- 全文大小：291 K
文摘
Lithiated anions derived from (alkenyl)pentamethyl phosphoric triamides as homoenolate equivalents are used in the reaction with halogenated acetal and ketal giving regioselectively the γ-alkylation adducts. Chemoselective acidic hydrolysis of the enephosphoramide moiety in the presence of acetal or ketal groups leads to expected carbonyl products, key intermediates in the synthesis of natural compounds. The synthetic potential of the presented strategy is illustrated by stereoselective synthesis of two pheromones namely, 9-oxo-2(E)-decenoic acid 1 from queen substance and 10-hydroxy-2(E)-decenoic acid 2 from royal jelly of honeybee Apis mellifera.