TY - JOUR
T1 - Asymmetric synthesis of (−)-dehydro-exo-brevicomin with a photoisomerisation-intramolecular acetalisation sequence
AU - Hirasawa, Shun
AU - Masuda, Tsuyoshi
AU - Mukai, Ken
AU - Miyoshi, Yusuke
AU - Kanomata, Nobuhiro
N1 - Funding Information:
The authors thank Ms Yuki Goda for performing some preliminary experiments for this project. The author NK would like to express his sincere gratitude for the financial support from Mitsubishi Materials Corporation and the Waseda University Faculty of Science and Engineering Comprehensive Agreement Research Grant.
Publisher Copyright:
© The Royal Society of Chemistry 2021.
PY - 2021/8/21
Y1 - 2021/8/21
N2 - 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.
AB - 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.
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U2 - 10.1039/d1ob00952d
DO - 10.1039/d1ob00952d
M3 - Article
C2 - 34328158
AN - SCOPUS:85112727316
SN - 1477-0520
VL - 19
SP - 6897
EP - 6903
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
IS - 31
ER -