Abstract
A convergent synthesis of four stereoisomers of the sex pheromone of the western corn rootworm (8-methyldecan-2-yl propionate, 1) from commercially available chiral starting materials is reported. The key step was Julia–Kocienski olefination between chiral BT-sulfone and chiral aldehyde. This synthetic route provided the four stereoisomers of 1 in 24–29% total yield via a six-step sequence. The simple scale-up strategy provides a new way to achieve the asymmetric synthesis of the sex pheromone.
Highlights
The BT-sulfone (S)-3 was synthesized in high yield from commercially available chiral alcohol
The expensive starting material (R)-5 was synthesized in 3 steps from Evans auxiliary [22] 9 with R configuration [23–26]
Synthesis of decreasing chiral aldehydes (S)-4 and (R)-4.All are in accordance with those reported in the literature
Summary
Modern agriculture means finding ways to increase production while being friendly to the environment, i.e., sustainable development. FOR PEERstudies, REVIEWwe developed a convergent synthetic route to the four stereoisomers. A number of different synthetic routes to 1 have been reported [5,9–12]. The enantioselective www.mdpi.com/journal/molecules by the chiral auxiliary strategy and HPLC resolution of diastereomers [13], enzyme-catalyzed reduction [14], and Sharpless asymmetric dihydroxylation [15]. In 1984, Mori synthesized (2S,8R)-1 and Molecules. 2018, doi:10.3390/molecules23030667 syntheses of, the667; four isomers was exploited. A number of different synthetic routes to 1 have have been been reported reported [5,9–12]. The enantioselective syntheses of the four isomers was exploited by the chiral auxiliary strategy and HPLC resolution of diastereomers [13], enzyme-catalyzed reduction [14], and Sharpless asymmetric dihydroxylation [15]. (2R,8R)-1 via synthesized (2S,8R)-1 by by a remote-controlled diastereoselective conjugated addition [17]. (2R,8R)-1 was obtained over a remote-controlled diastereoselective conjugated addition [17].
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