tert-butyl (5R)-5-(acetoxy)hexanoate → (1S,2E)-3-{(1R,2R,3S,5R)-2-[(2Z)-7-(ethylamino)-7-oxohept-2-en-1-yl]-3,5-dihydroxycyclopentyl}-1-(2-phenylethyl)prop-2-en-1-yl (5R)-5-(nitrooxy)hexyl carbonate

Participants

Reaction Steps

Similar to Example R-1, except started Scheme R with antipodal tert-butyl (5R)-5-(acetoxy)hexanoate (Pamies, O.; Backvall, J.-E. J. Org. Chem. 2002, 67, 1261-1265) and eventually prepared antipode of crude p-nitrophenyl carbonate r-4, which was similarly used to acylate bimatoprost boronate (580 mg, 1.2 mmol) to provide after preparative HPLC purification, 420 mg (57%) of 15-acyl nitrate R-2.

Provenance & Evidence