Synthesis of an angularly fused tricycle via tandem ring closing metathesis.; Tricycles, triquinanesSyntheticPage 198 (2002)
Submitted 29th Jul 2002, published 30th Jul 2002
A contribution from the Harrity Group, University of Sheffield
Dichloroethane (DCE), distilled over CaH2, Grubbs’ catalyst, Lancaster
A solution of anti 1R*, 2, 2, 3R*-tetraallylcyclopentanediol 1 (50 mg, 0.19 mmol) was dissolved in dry, distilled DCE (2 ml). Grubbs’ catalyst [Ru(PCy3)2Cl2(CHPh)] (8 mg, 0.0095 mmol) in DCE (1 ml) was added via syringe. The reaction mixture was heated to 60 oC under N2 overnight. A further 5 mol% of Grubbs’ catalyst was added after 24 h. In total, 10 mol% of Grubbs catalyst had been added over 48 h with heating throughout. The solvent was removed in vacuo and purification on silica gel using 2:1 hexane:EtOAc supplied the desired tricycle 2 as a pale yellow oil. (28 mg, 72%)
We have carried out many tandem ring closing metathesis reactions, and have found the catalyst to be very robust and reliable. On some of our other systems slightly higher catalyst loadings have been required to complete the conversion. The scale of the reaction does not seem to be important with 50mg reactions working as well as 1g reactions. Also, it is worth taking some care with the chromatographic purification of reactions using Ru catalysts as they have a habit of sticking to your compound. If necessary reduce the polarity of the column to overcome this problem.
1H-NMR (250 MHz, CDCl3): d 1.60 (2H, br s, OH), 1.70-2.04 (6H, m) 2.14-2.38 (4H, m), 2.46-2.58 (2H, m), 5.54-5.71 (4H, m).
13C-NMR (62.9 MHz, CDCl3): d 33.5, 35.3, 39.1, 61.3, 80.8, 125.0, 125.7.
Bassindale, M.J., Edwards, A.S., Hamley, P., Adams, H., Harrity, J.P.A., Chem. Commun., 2000, 1035.
For recent metathesis reviews see: Grubbs, R.H., Chang, S., Tetrahedron, 1998, 54, 4413; Fürstner, A., Angew. Chem., Int. Ed. Engl., 2000, 39, 3012.
This page has been viewed approximately 800 times since records began.
Get CDX file (Choose "Open this file from its current location" TWICE)
SyntheticPagesTM are for use
exclusively by those with training and experience in synthetic chemistry. While contributors
are asked to identify hazards and to use methods designed to reduce risk, no formal hazard
or risk assessments are included, and these procedures must be conducted at one's own risk.
SyntheticPages, its editors, owners and associates do not warrant or guarantee the safety of
individuals using these procedures and hereby disclaim any liability for any injuries or damages
claimed to have resulted from or related in any way to the procedures herein. Copyright ©2005 Synthetic Pages
Comment on this page!
Registered users may add comments to other pages. If you have already registered, please
log in, otherwise you may
Back to List