期刊
TETRAHEDRON
卷 68, 期 7, 页码 1936-1946出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.12.064
关键词
Acanthoscelides obtectus (Say); Allene; Claisen rearrangement; Heck reaction; Lipase; Optically active allene; Pheromone
资金
- Toyo Gosei Co., Ltd
The enantiomers of methyl (E)-2,4,5-tetradecatrienoate (1), a component of the male pheromone of Acanthoscelides obtectus, were synthesized from the enantiomers of 1-undecyn-3-ol (6), which were obtained via asymmetric acetylation of (+/-)-1-trimethylsilyl-1-undecyn-3-ol (4) with vinyl acetate as catalyzed by lipase PS (Amano). The ortho ester Claisen rearrangement of 6 with triethyl orthoacetate was the key-step to generate the chiral allenic system. A new synthesis of (+/-)-1 was also executed starting from (+/-)-6. Three different syntheses of methyl (2E,4Z)-2,4-decadienoate (2), another component of the male pheromone of A. obtectus, were achieved by means of either palladium-catalyzed Heck reaction or a Claisen and an Al2O3 catalyzed thermal rearrangements. (C) 2011 Elsevier Ltd. All rights reserved.
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