Asymmetric synthesis of (−)-dehydro-exo-brevicomin with a photoisomerisation–intramolecular acetalisation sequence. Issue 31 (30th July 2021)

• Record Type: Journal Article
• Authors: Hirasawa, Shun; Masuda, Tsuyoshi; Mukai, Ken; Miyoshi, Yusuke; Kanomata, Nobuhiro
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 31(2021)
• Page Start: 6897
• Page End: 6903
• Publication Date: 2021-07-30
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob00952d
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : We have accomplished the asymmetric synthesis of (−)-dehydro- exo -brevicomin in a practical and scalable manner via a possible biosynthetic precursor obtained by photoisomerisation. 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 5 in situ, the possible biosynthetic precursor of DHB.