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 fromtrans-3-hexen-1-ol (7). We successfully prepared the target molecule (−)-1from spontaneous intramolecular acetalisation after the photoisomerisation oftrans-enone6, which generated the correspondingcis-enone5in situ, the possible biosynthetic precursor of DHB.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry