SYNTHESIS AND THE DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF MATSUONE, SEX-PHEROMONE OF FEMALE MATSUCOCCUS PINE SCALES

Authors
SHI XW WEBSTER FX MEINWALD J
Citation
Xw. Shi et al., SYNTHESIS AND THE DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF MATSUONE, SEX-PHEROMONE OF FEMALE MATSUCOCCUS PINE SCALES, Tetrahedron letters, 36(40), 1995, pp. 7201-7204
Citations number
8
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
40
Year of publication
1995
Pages
7201 - 7204
Database
ISI
SICI code
0040-4039(1995)36:40<7201:SATDOT>2.0.ZU;2-U
Abstract
The four possible optical isomers of matsuone (1), female sex pheromon e of Matsucoccus resinosae pine scales, were convergently synthesized in high optical purities. The absolute configuration of the natural pr oduct has been assigned as 10R)-4,6,10,12-tetramethyltridecan-2,4-dien -7-one. Bioassays with M. resinosae using these stereoisomers reveal t hat the unnatural (6R, 10S)-isomer mimics the natural pheromone.