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J Org Chem

Title:		"A new route to methyl (R,E)-(-)-tetradeca-2,4,5-trienoate (pheromone of Acanthoscelides obtectus) utilizing a palladium-catalyzed asymmetric allene formation reaction"
Author(s):		Ogasawara M; Nagano T; Hayashi T;
Address:		"Catalysis Research Center and Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita-ku, Sapporo 001-0021, Japan. ogasawar@cat.hokudai.ac.jp"
Journal Title:		J Org Chem
Year:		2005
Volume:		70
Issue:		14
Page Number:		5764 - 5767
DOI:		10.1021/jo050684z
ISSN/ISBN:		0022-3263 (Print) 0022-3263 (Linking)
Abstract:		"[reaction: see text] A formal total synthesis of the sex attractant of male dried bean beetle, methyl (R,E)-(-)-tetradeca-2,4,5-trienoate, was achieved by a new efficient route utilizing the Pd-catalyzed asymmetric allene synthesis reaction. It was found that the atropisomeric biaryl bisphosphine (R)-segphos showed better enantioselectivity than (R)-binap in the Pd-catalyzed reaction for preparing alkyl-substituted axially chiral allenes"
Keywords:		Alkadienes/*chemistry Animals Catalysis *Coleoptera Molecular Structure Palladium/*chemistry Pheromones/chemical synthesis Phosphines/chemistry Stereoisomerism;
Notes:		"MedlineOgasawara, Masamichi Nagano, Takashi Hayashi, Tamio eng Research Support, Non-U.S. Gov't 2005/07/02 J Org Chem. 2005 Jul 8; 70(14):5764-7. doi: 10.1021/jo050684z"