Vinylcyclopentane → (3R,4R,5S)-5-[(1R,2E)-3-cyclopentyl-1-hydroxyprop-2-en-1-yl]-4-hydroxy-3-methoxydihydrofuran-2(3H)-one

Participants

Reaction Steps

2 g of 31 (10.63 mmol), 4.22 g of vinylcyclopentane (43.92 mmol), 80 mL of CH2Cl2 and 226 mg of 2nd generation Grubb's catalyst (C46H65Cl2N2PRu, MW 848.98, 0.266 mmol) are added to a 250 mL round-bottomed flask. The medium is stirred for 2 h at RT and then heated for 4 h at 45° C. The insoluble material is filtered and then the solvent is evaporated and the crude product (3.39 g) is chromatographed on a silica cartridge (150 g), eluting with a heptane/AcOEt (50/50) mixture. 1.39 g of expected product 32 (white solid) are obtained.

Provenance & Evidence