Issue 31, 2021

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

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
16 May 2021
Accepted
14 Jul 2021
First published
23 Jul 2021

Org. Biomol. Chem., 2021,19, 6897-6903

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

S. Hirasawa, T. Masuda, K. Mukai, Y. Miyoshi and N. Kanomata, Org. Biomol. Chem., 2021, 19, 6897 DOI: 10.1039/D1OB00952D

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