Determination of the absolute configuration of the male aggregation pheromone, 2-methyl-6-(4′-methylenebicyclo[3.1.0]hexyl)hept-2-en-1-ol, of the stink bug Erysarcoris lewisi (Distant) as 2Z,6R,1′S,5′S by its synthesis

被引：8

作者：

Mori, Kenji ^{[1
,2
]}

Tashiro, Takuya ^{[2
]}

Yoshimura, Tomoko ^{[3
]}

Takita, Masami ^{[4
]}

Tabata, Jun ^{[5
]}

Hiradat, Shyuntaro ^{[5
]}

Sugie, Hajime ^{[5
]}

机构：

[1] Toyo Gosei Co Ltd, Photosensit Mat Res Ctr, Inba, Chiba 2701609, Japan

[2] RIKEN, Res Ctr Allergy & Immunol, Glycosphingolipid Synthesis Grp, Lab Immune Regulat, Wako, Saitama 3510798, Japan

[3] Yamagata Gen Agar Res Ctr, Yamagata 9902732, Japan

[4] Magami Area Gen Branch, Ind & Econ Affairs Dept, Agr Tech Popularizat Div, Yamagata 9902732, Japan

[5] Natl Inst Agroenvironm Sci, Tsukuba, Ibaraki 305, Japan

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 02期

关键词：

CD; Erysarcoris lewisi; lipase; pheromone; sesquisabinen-1-ol;

D O I：

10.1016/j.tetlet.2007.11.036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lipase-catalyzed asymmetric acetylation of a mixture of (6R,1'S,4'S,5'R)- and (6R,1'R,4'R,5'S)-7'-norsesquisabinen-4'-ol (3) afforded a separable mixture of the recovered former and the acetate of the latter. The recovered alcohol was oxidized to (6R,1'S,5'R)-sesquisabina ketone (2), whose absolute configuration could be assigned by its CD comparison with (1R,5S)-sabina ketone (4). Conversion of (6R,1'S,5'R)-sesquisabina ketone (2) to the bioactive pheromone revealed the stereostructure of the male aggregation pheromone of the stink bug Erysarcoris lewisi (Distant) to be (2Z,6R,1'S,5'S)-2-methyl-6-(4'-methylenebicyclo[3.1.0]hexyl)hept-2-en-1-ol (sesquisabinen-1-ol, 1). (C) 2007 Elsevier Ltd. All rights reserved.

引用

页码：354 / 357

页数：4

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