Washington State University

Ethyl Corporation

Donald S Matteson

Gordon G Knapp

William E Wright

Bryan T Davis

Gerald D Hurst

Rajendra P Singh

Hon-Wah Man

Oliver Ho

Kizhakethil M Sadhu

Serricornin, the attractant pheromone of the cigarette beetle, is synthesized in high enantiomeric and diastereomeric purity via a series of reactions of asymmetric 2-(1-haloalkyl)-1,3,2-dioxaborolanes with Grignard reagents, which lead to the key intermediate �,S-(R*,R*,R*)!-2-ethyl-3,5-dimethyl-l-octen-6-ol. Oxidative cleavage of the carbon-carbon double bond of �S-(R*,R*,R*)!-2-ethyl-3,5-dimethyl-l-octen -6-ol with osmium tetroxide and sodium periodate yields serricornin.

Stereocontrolled synthesis of serricornin

A method of synthesis of (2S,3R,1'R)-stegobinone(I) using borane intermediates and methods for the use of stegobinone (I) for attracting beetles of the Anobium species.

Method for the stereocontrolled synthesis of stegobinone and useful

An additive composition of boronated phenolic antioxidant and anti-haze diol capable of complexing with boric acid as well as organic material protected by the additive composition. A hydrolytically stable additive composition comprising a boronated phenolic antioxidant and a diol member capable of reacting with boric acid formed as a hydrolysis product to form a stable ring structure soluble in a substrate. The additive composition prevents or cures a haze caused by hydrolysis.

Haze-free boronated antioxidant

Esters of .alpha.,.alpha.-haloalkyl boronic acids are prepared by the addition of an alkali metal dialkylamide, or some other equivalent sterically hindered base to a mixture of a 1,1-dihaloalkane and a trialkyl borate in an organic solvent at a temperature between about -78.degree. C. and +25.degree. C. In one embodiment, diisopropyl (dichloromethyl)borate is formed by the addition of lithium diisopropylamide to a mixture of dichloromethane and triisopropyl borate in the presence of tetrahydrofuran as the solvent medium at a temperature between about -10.degree. C. and +10.degree. C.

Preparation of .alpha.,.alpha.-dihaloalkyl boronic esters

Boronate complexes are rearranged in the presence of a Lewis acid catalyst to boronic esters, particularly .alpha.-haloboronic esters.

Growing community of inventors

Moscow, ID, United States of America

Donald S Matteson