A novel polyfunctional chiral building block derived from (<i>S</i>)-ethyl lactate. Application to the synthesis of the sex pheromone of the southern corn rootworm (<i>Diabrotica undecimpunctata howardi</i>)期刊界 All Journals 搜尽天下杂志传播学术成果专业期刊搜索期刊信息化学术搜索

*A novel polyfunctional chiral building block derived from (S)-ethyl lactate. Application to the synthesis of the sex pheromone of the southern corn rootworm (Diabrotica undecimpunctata howardi)*

Authors:	M. V. Zlokazov and V. V. Veselovsky

Affiliation:	(1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913 Moscow, Russian Federation

Abstract:	Highly enantiomerically pure (4S, 5E)-4-bromomethylhept-5-enenitrile was prepared from (S)-ethyl lactate by a six-step procedure involving a rearrangement of chiral cyclopropylcarbinol. This product was used for the synthesis of the sex pheromone of the southern corn rootworm (Diabrotica undecimpunctata howardi), (10R)-10-methyltridecan-2-one. For preliminary communication, see Ref. 1. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 151–155, January, 2000.

Keywords:	(S)-(− )-ethyl lactate allylic alcohol diastereoselective cyclopropanation Julia— Johnson rearrangement chiral cyclopropylcarbinol (4S, 5E)-4-bromomethyl-5-enenitrile (10R)-10-methyltridecan-2-one sex pheromone southern corn rootworm (Diabrotica undecimpunctata howardi)
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