(6aR,7S,9aS,13aS)-5-benzyloxy-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-6a,7,10,10-tetramethyl-11-(1-oxa-4-azacyclohex-4-yl)imino-3-oxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindole → (6aR,7S,9aS,13aS)-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-5-hydroxy-6a,7,10,10-tetramethyl-11-(1-oxa-4-azacyclohex-4-yl)imino-3-oxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindole

Participants

Reaction Steps

To a solution of Compound (61) (224 mg, 0.40 mmol) in 50 ml of methanol containing 1% water was added 180 mg of 10% palladium-carbon, followed by catalytic reduction. After the palladium-carbon was removed by filtration, the filtrate was concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (silica gel 10 g; ethyl acetate:methanol=99:1) and further crystallization from diethyl ether-n-hexane to give 152 mg (79%) of Compound (51f).

Provenance & Evidence