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Org Biomol Chem

Title:		Asymmetric synthesis of (-)-dehydro-exo-brevicomin with a photoisomerisation-intramolecular acetalisation sequence
Author(s):		Hirasawa S; Masuda T; Mukai K; Miyoshi Y; Kanomata N;
Address:		"Department of Chemistry and Biochemistry, Waseda University, Shinjuku-ku, Tokyo 169-8555, Japan. kanomata@waseda.jp"
Journal Title:		Org Biomol Chem
Year:		2021
Volume:		19
Issue:		31
Page Number:		6897 - 6903
DOI:		10.1039/d1ob00952d
ISSN/ISBN:		1477-0539 (Electronic) 1477-0520 (Linking)
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"
Keywords:
Notes:		"PubMed-not-MEDLINEHirasawa, Shun Masuda, Tsuyoshi Mukai, Ken Miyoshi, Yusuke Kanomata, Nobuhiro eng Research Support, Non-U.S. Gov't England 2021/07/31 Org Biomol Chem. 2021 Aug 11; 19(31):6897-6903. doi: 10.1039/d1ob00952d"