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Proc Natl Acad Sci U S A

Title:		Stereoisomer libraries: total synthesis of all 16 stereoisomers of the pine sawfly sex pheromone by a fluorous mixture-synthesis approach
Author(s):		Dandapani S; Jeske M; Curran DP;
Address:		"Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA"
Journal Title:		Proc Natl Acad Sci U S A
Year:		2004
Volume:		20040524
Issue:		33
Page Number:		12008 - 12012
DOI:		10.1073/pnas.0401677101
ISSN/ISBN:		0027-8424 (Print) 1091-6490 (Electronic) 0027-8424 (Linking)
Abstract:		"All 16 stereoisomers of the sex pheromone of pine sawfly (3,7,11-trimethylundecanol propanoate ester) have been synthesized on a 10- to 20-mg scale by a split-parallel fluorous mixture-synthesis approach. Spectral data obtained for all 32 compounds (16 alcohols and the corresponding propionates) matched well with published data, thereby validating the fluorous-tag encoding of diastereoisomers. This fluorous-tag encoding method is recommended for the efficient synthesis of multiple stereoisomers for spectroscopic studies, biological tests, or other structure-function relationships"
Keywords:		"Animals Chemistry, Organic/methods Female Fluorine/chemistry Hymenoptera Magnetic Resonance Spectroscopy Molecular Structure Sex Attractants/*chemical synthesis/*chemistry Stereoisomerism;"
Notes:		"MedlineDandapani, Sivaraman Jeske, Mario Curran, Dennis P eng Research Support, U.S. Gov't, P.H.S. 2004/05/26 Proc Natl Acad Sci U S A. 2004 Aug 17; 101(33):12008-12. doi: 10.1073/pnas.0401677101. Epub 2004 May 24"