Asymmetric synthesis of (-)-dehydro-exo-brevicomin with a photoisomerisation-intramolecular acetalisation sequence
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Updated: Oct 26, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
Shun Hirasawa1, Tsuyoshi Masuda1, Ken Mukai1
1Department of Chemistry and Biochemistry, Waseda University, Shinjuku-ku, Tokyo 169-8555, Japan. kanomata@waseda.jp.
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 5in situ, the possible biosynthetic precursor of DHB.
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