Asymmetric synthesis of (−)-dehydro-exo-brevicomin with a photoisomerisation-intramolecular acetalisation sequence

Shun Hirasawa, Tsuyoshi Masuda, Ken Mukai, Yusuke Miyoshi, Nobuhiro Kanomata*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


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.

Original languageEnglish
Pages (from-to)6897-6903
Number of pages7
JournalOrganic and Biomolecular Chemistry
Issue number31
Publication statusPublished - 2021 Aug 21

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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