Abstract
2,3-Butanediacetal derivatives were used for the stereoselective synthesis of unsymmetrically substituted cis-epoxides. The procedure was applied for the preparation of both enantiomers of disparlure and monachalure, the components of the sex pheromones of the gypsy moth (Lymantria dispar) and the nun moth (Lymantria monacha) using methyl (2S,3R,5R,6R)-3-ethylsulfanylcarbonyl-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2-carboxylate as the starting material.
Highlights
Compounds containing chiral epoxides display a wide range of biological activities and a number of them are semiochemicals. They have been frequently found as pheromones in lepidopteran species of the families Noctuidae, Arctiidae, Lymantridae, Geometridae and Erebidae [1]. (3Z,9Z)-6S,7REpoxyheneicosa-3,9-diene, a constituent of the female sex pheromone of the moth Tetanolita mynesalis (Erebidae) [2] is a interesting example, because it is a component of the luring mixture used by the bolas spider Mastophora hutchinsoni [3,4]. (6R,7S,2E)-6,7-Epoxy-2-nonenal has been identified as a sex-aggregation pheromone of the red-necked longhorn beetle (Aromia bungii) [5] and its synthesis has been recently developed by Mori and co-workers [6,7]. (2E)-trans4,5-Epoxy-2-decenal is present in mammalian blood and may be used by predators to track their prey [8,9]
Most recently a method using the asymmetric chlorination of dodecanal by LiCl in the presence of a chiral imidazolidinone catalyst has been described [29]. Many of these methods have some drawbacks – the most important one being the insufficient enantiomeric purity for biological and commercial applications [29]. (+)-Disparlure used in most commercial lures is prepared by the Sharpless epoxidation reaction, which gives the final product with ees not exceeding 95% [29], which is insufficient to be used as attractant for males of the Gypsy moth
A few methods for the synthesis of diols 5 and 7 have been described [26,30,31] and we decided to prepare them starting from 2,3-butanediacetal derivatives of ʟ-tartaric acid
Summary
Compounds containing chiral epoxides display a wide range of biological activities and a number of them are semiochemicals. (+)-Disparlure used in most commercial lures is prepared by the Sharpless epoxidation reaction, which gives the final product with ees not exceeding 95% [29], which is insufficient to be used as attractant for males of the Gypsy moth. A few methods for the synthesis of diols 5 and 7 have been described [26,30,31] and we decided to prepare them starting from 2,3-butanediacetal derivatives of ʟ-tartaric acid.
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