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

Participants

Reaction Steps

400 mg of 31 (2.13 mmol), 1.56 g of 2-bromostyrene (8.5 mmol), 1 mL of THF, 16 mL of CH2Cl2 and 54 mg of 2nd generation Grubb's catalyst (C46H65Cl2N2PRu, MW 848.98, 0.06 mmol) are added to a 100 mL round-bottomed flask. The medium is stirred for 24 h at RT. The solvent is evaporated, the crude product (1.9 g) is chromatographed on a silica cartridge (90 g), eluting with a CH2Cl2/MeOH (95/5) mixture. 190 mg of expected product 45 are obtained.

Provenance & Evidence