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J Org Chem

Title:		"An efficient synthesis of (+/-)-grandisol featuring 1,5-enyne metathesis"
Author(s):		Graham TJ; Gray EE; Burgess JM; Goess BC;
Address:		"Department of Chemistry, Furman University, 3300 Poinsett Highway, Greenville, South Carolina 29613, USA"
Journal Title:		J Org Chem
Year:		2010
Volume:		75
Issue:		1
Page Number:		226 - 228
DOI:		10.1021/jo9020375
ISSN/ISBN:		1520-6904 (Electronic) 0022-3263 (Print) 0022-3263 (Linking)
Abstract:		"An eight-step synthesis of (+/-)-grandisol features a key sequence involving a high-yielding, microwave-assisted enyne metathesis to yield a 1-alkenylcyclobutene that is semihydrogenated to yield a silyl-protected grandisol. Metathesis catalyst screens revealed an intriguing trend whereby substrate conversion correlated strongly with the identity of the ligands on the catalyst. In addition, new reactivity of 1-alkenylcyclobutenes toward hydrogenation is described"
Keywords:		Alkynes/*chemistry Catalysis Molecular Structure Sex Attractants/*chemical synthesis/chemistry Stereoisomerism Terpenes/*chemical synthesis/chemistry;
Notes:		"MedlineGraham, Thomas J A Gray, Erin E Burgess, James M Goess, Brian C eng P20 RR016461-095761/RR/NCRR NIH HHS/ P20 RR016461-066796/RR/NCRR NIH HHS/ P20 RR016461/RR/NCRR NIH HHS/ P20 RR-016461/RR/NCRR NIH HHS/ P20 RR016461-077044/RR/NCRR NIH HHS/ P20 RR016461-086525/RR/NCRR NIH HHS/ Research Support, N.I.H., Extramural Research Support, Non-U.S. Gov't 2009/12/05 J Org Chem. 2010 Jan 1; 75(1):226-8. doi: 10.1021/jo9020375"