HCID 15219011, compound → (2S,4S,5S)-5-benzyloxycarbonylamino-6-cyclohexyl-2-isopropyl-4-hexanolide

Participants

Reaction Steps

A solution of diol prepared in Example 19 (500 mg, 1.3 mmol) and Jones Reagent 2.7M (1.9 mL, 5.2 mmol) in 10 mL acetone was stirred vigorously at 10° C. for 3 hours. The reaction mixture was filtered through a plug of Celite® and the plug was washed repeatedly with diethyl ether. The ether layer was washed 2×5 mL with saturated brine, dried over MgSO4 and concentrated in vacuo to give a white solid. The solid was flash chromatographed on silica eluting with 20% EtOAc/80% hexanes to give 286 mg (57%) of the title compound which was identical to the lactone prepared in Example 24.

Provenance & Evidence