(6aR,7S,9aS, 11R,12S,13aS)-5-benzyloxy-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-11,12-dihydroxy-6a,7,10,10-tetramethyl-3-oxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindole → (6aR,7S,9aS, 11R,12S,13aS)-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-5,11,12-trihydroxy-6a,7,10,10-tetramethyl-3-oxo-1H-benzo[8,8a][l]benzopyrano[2,3-e]isoindole

HRID 1417623Notes

Reaction equation

HRID 1417623 reaction equation
C([O:8][C:9]1[C:10]2[CH2:22][C@:21]3([CH3:36])[C@@H:23]([CH3:35])[CH2:24][CH2:25][C@H:26]4[C:27]([CH3:34])([CH3:33])[C@@H:28]([OH:32])[C@@H:29]([OH:31])[CH2:30][C@@:20]34[O:19][C:11]=2[C:12]2[CH2:13][NH:14][C:15](=[O:18])[C:16]=2[CH:17]=1)C1C=CC=CC=1>CO.[C].[Pd]>[OH:8][C:9]1[C:10]2[CH2:22][C@:21]3([CH3:36])[C@@H:23]([CH3:35])[CH2:24][CH2:25][C@H:26]4[C:27]([CH3:34])([CH3:33])[C@@H:28]([OH:32])[C@@H:29]([OH:31])[CH2:30][C@@:20]34[O:19][C:11]=2[C:12]2[CH2:13][NH:14][C:15](=[O:18])[C:16]=2[CH:17]=1

Participants

4

Reactant 1

HCID 86753825(6aR,7S,9aS, 11R,12S,13aS)-5-benzyloxy-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-11,12-dihydroxy-6a,7,10,10-tetramethyl-3-oxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindole

Product 1

HCID 86753826(6aR,7S,9aS, 11R,12S,13aS)-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-5,11,12-trihydroxy-6a,7,10,10-tetramethyl-3-oxo-1H-benzo[8,8a][l]benzopyrano[2,3-e]isoindoleYield 91%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To Compound (49a) (43 mg, 0.088 mmol) dissolved in 3.0 ml of methanol was added 9 mg of palladium-carbon, and the mixture stirred under hydrogen atmosphere for 2 hours at room temperature. After the palladium-carbon was removed by filtration, the filtrate was concentrated under reduced pressure. The residue was purified by a preparative thin layer chromatography (Merck, Kieselgel 60 F254, 0.5 mm; chloroform:methanol=10:1) and further by crystallization from diethyl ether to give 32 mg (91%) of Compound (50a).

Workup

  1. customAfter the palladium-carbon was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by a preparative thin layer chromatography (Merck, Kieselgel 60 F254, 0.5 mm; chloroform:methanol=10:1) and further by crystallization from diethyl ether

Sources & evidence

ORD record
ord-4ef6442f6dee483e92a568f25253bee1
Source dataset
uspto-grants-1999_03
Patent number
US05876984

Reaction notes

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