Insect Pheromones. Stereoselective Reduction of β- or ω-Alkynols to the Corresponding (E)-Alkenols by Lithium Tetrahydroaluminate
- 1 January 1977
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1977 (08) , 561-562
- https://doi.org/10.1055/s-1977-24474
Abstract
Redn. of RC≡C(CH2)nOH (I; n, R given; 7, MeCHEt(CH2)4; 2, hexyl; 6, Bu; 6, octyl) with LiAlH4 in diglyme-THF gave 85-94% E-RCH:CH(CH2)nOH (II). I (n, R given; 7, MeCHEt(CH2)4; 6, Bu; 6, octyl) were prepd. by reaction of RC≡CLi with the resp. (tetrahydropyranyloxy)iodoalkane. The acetate of II (R = Bu, n = 6) is the sex pheromone of the false codling moth, Argyroploce leucotretaKeywords
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