Asymmetric synthesis of (−)-dehydro-exo-brevicomin with a photoisomerisation–intramolecular acetalisation sequence. Issue 31 (30th July 2021) - Hirasawa, Shun
Abstract : We have accomplished the asymmetric synthesis of (−)-dehydro- exo -brevicomin in a practical and scalable manner via a possible biosynthetic precursor obtained by photoisomerisation. Abstract : We herein report a novel, short asymmetric synthesis of (−)-dehydro- exo -brevicomin (DHB, 1 ), a sex pheromone isolated from house mice, in 44% overall yield, the highest yield reported so far, over eight steps from trans -3-hexen-1-ol (7 ). We successfully prepared the target molecule (−)-1 from spontaneous intramolecular acetalisation after the photoisomerisation of trans -enone 6, which generated the corresponding cis -enone 5 in situ, the possible biosynthetic precursor of DHB.