Journal of Chemical Ecology p. 673 - 680 (1996)
Update date:2022-08-10
Topics:
Razkin
Gil
Gonzalez
Dominicalure 1 (9a) and dominicalure 2 (9b), were synthesized by esterification of α,β-unsaturated acids 4a and 4b with (5)-(+)-2-pentanol (8). The key step was the asymmetric reduction of 3-penten-2-one (5) to give the chiral intermediate 6, which, upon diimide reduction, DNB derivatization, recrystallization, and hydrolysis, yielded 8 in 63% ee. Acids 4a and 4b were prepared in a simple and efficient three-step synthesis with an overall yield of 54% and 62%, respectively, in stereoisomerically pure form.
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