Synthesis of (3S,4S)-4-Methyl-3-heptanol and Its (3S,4R)-Isomer Employing Asymmetric Epoxidation Coupled with Regioselective Cleavage of Epoxides with Trimethylaluminum
- 1 October 1984
- journal article
- research article
- Published by Oxford University Press (OUP) in Agricultural and Biological Chemistry
- Vol. 48 (10), 2505-2510
- https://doi.org/10.1080/00021369.1984.10866523
Abstract
(3S,4S)-( – )-4-Methyl-3-heptanol, the key compound in the aggregation pheromone of Scolytus multistriatus Marsham, was synthesized by employing asymmetric epoxidation and epoxide cleavage with trimethylaluminum as the key steps. (3S,4S)-( + )-4-Methyl-3-heptanol was also synthesized.This publication has 6 references indexed in Scilit:
- The stereoisomeric composition of the 4-methyl-3-heptanol produced by Scolytus scolytus and the preparation and biological activity of the four synthetic stereoisomersInsect Biochemistry, 1979
- Volatiles associated with unmated Scolytus scolytus beetles on english elm: Differential production of α-Multistriatin and 4-methyl-3-heptanol, and their activities in a laboratory bioassayInsect Biochemistry, 1978
- Pheromone synthesis. 6. A synthesis of (-)-.alpha.-multistriatinThe Journal of Organic Chemistry, 1977
- Absolute configuration of (−)-4-methylheptan-3-ol, a pheromone of the smaller european elm bark beetle, as determined by the synthesis of its (3R,4R)-(+)- and (3S,4R)-(+)-isomersTetrahedron, 1977
- Synthesis and absolute configuration of multistriatinThe Journal of Organic Chemistry, 1976
- “P-2 nickel” catalyst with ethylenediamine, a novel system for highly stereospecific reduction of alkynes to cis-olefinsJournal of the Chemical Society, Chemical Communications, 1973