Ultrasound Assisted Synthesis of 5,9-Dimethylpentadecane and 5,9-Dimethylhexadecane – the Sex Pheromones of Leucoptera coffeella 英文参考文献.docVIP

Molecules 2007, 12, 2080- 2088 molecules ISSN 1420-3049 ? 2007 by MDPI /molecules Full Paper Ultrasound Assisted Synthesis of 5,9-Dimethylpentadecane and 5,9-Dimethylhexadecane – the Sex Pheromones of Leucoptera coffeella Nhuan Ngoc Doan 1,§, Thach Ngoc Le 2, Hao Cong Nguyen 3, Poul Erik Hansen 1 and Fritz Duus 1,* 1 Department of Science, Systems and Models, Roskilde University, P. O. Box 260, DK-4000 Roskilde, Denmark; E-mails: dnnhuan@.vn, poulerik@ruc.dk 2 Department of Organic Chemistry, University of Natural Sciences, National University of Ho Chi Minh City, 227 Nguyen Van Cu, Ho Chi Minh City, Vietnam; E-mail: lenthach@hcm.vnn.vn 3 Institute of Natural Products Chemistry of Ho Chi Minh City, 01 Mac Dinh Chi, Ho Chi Minh City, Vietnam; E-mail: nguyenconghao@ § On leave from the University of Natural Sciences, National University of Ho Chi Minh City, Vietnam. * Author to whom correspondence should be addressed; E-mail: fd@ruc.dk. Received: 8 August 2007; in revised form: 23 August 2007 / Accepted: 23 August 2007 / Published: 28 August 2007 Abstract: Racemic 5,9-dimethylpentadecane and 5,9-dimethylhexadecane, the major and minor constituents, respectively, of the sex pheromone of Leucoptera coffeella, have been synthesized from citronellol in 56-58% overall yield through six steps. Ultrasound irradiation efficiently supported tosylation of alcohols (two steps) as well as the subsequent cross coupling reactions with the pertinent Grignard reagents (also two steps). Keywords: 5,9-Dimethylpentadecane; 5,9-Dimethylhexadecane; Ultrasound irradiation; Pheromones; Leucoptera coffeella.  Molecules 2007, 12 2081 Introduction Recent research has shown that several hydrocarbons with a 1,5-dimethyl skeleton are insect pheromones [1]. 5,9-Dimethylpentadecane (1) and 5,9-dimethylhexadecane (2) are known as the major and minor constituents, respectively, of the sex pheromone of Leucoptera coffeella, a pest of coffee trees [2]