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Copyright Syntheticpages ©2001

Synthesis of an angularly fused tricycle via tandem ring closing metathesis.; Tricycles, triquinanes

SyntheticPage 198 (2002)
Submitted 29th Jul 2002, published 30th Jul 2002

Andrew Edwards (,
A contribution from the Harrity Group, University of Sheffield

Reaction Scheme

Chemicals Used
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%)

Author's Comments
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.

Lead Reference
Bassindale, M.J., Edwards, A.S., Hamley, P., Adams, H., Harrity, J.P.A., Chem. Commun., 2000, 1035.

Other References
For recent metathesis reviews see: Grubbs, R.H., Chang, S., Tetrahedron, 1998, 54, 4413; Fürstner, A., Angew. Chem., Int. Ed. Engl., 2000, 39, 3012.

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