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Org Lett

Title:		"Efficient intramolecular asymmetric reductions of alpha-, beta-, and gamma-keto acids with diisopinocampheylborane"
Author(s):		Ramachandran PV; Brown HC; Pitre S;
Address:		"Herbert C. Brown Center for Borane Research, Purdue University, West Lafayette, Indiana 47907-1393, USA. chandran@purdue.edu"
Journal Title:		Org Lett
Year:		2001
Volume:		3
Issue:		1
Page Number:		17 - 18
DOI:		10.1021/ol0062291
ISSN/ISBN:		1523-7060 (Print) 1523-7052 (Linking)
Abstract:		"[figure: see text] alpha-, beta-, and gamma-Keto acids are reduced with diisopinocampheylborane at room temperature to the corresponding hydroxy acids with predictable stereochemistry in very high ee. The gamma-hydroxy acids produced were conveniently cyclized to the corresponding lactones. This provides a simple synthesis of 4-hexanolide, a component of the pheromone secreted by the female dermestid beetle Trogoderma glabrum"
Keywords:		Animals Boron Compounds/*chemistry Catalysis Coleoptera Female Keto Acids/*chemistry Lactones/*chemical synthesis/*chemistry Molecular Conformation Molecular Structure *Pheromones/chemistry/metabolism;
Notes:		"MedlineRamachandran, P V Brown, H C Pitre, S eng Research Support, U.S. Gov't, Non-P.H.S. 2001/06/30 Org Lett. 2001 Jan 11; 3(1):17-8. doi: 10.1021/ol0062291"