Asymmetric synthesis of (?)-dehydro-exo-brevicomin with a photoisomerisation–intramolecular acetalisation sequence?
Organic & Biomolecular Chemistry Pub Date: 2021-07-23 DOI: 10.1039/D1OB00952D
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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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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