HCID 69893717, compound → HCID 12990580, compound

HRID 2087017Notes

Reaction equation

HRID 2087017 reaction equation
[CH3:1][C@@:2]12[CH2:14][CH2:13][C@@H:12]3[C@:7]([CH3:17])([CH2:8][CH2:9][CH2:10][C:11]3([CH3:16])[CH3:15])[C@@H:6]1[C@@H:5]([OH:18])[CH:4]([OH:19])[O:3]2.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4]>C1C=CC=CC=1.C(OCC)C>[CH:4]([O:3][C@:2]1([CH3:1])[CH2:14][CH2:13][C@@H:12]2[C@:7]([CH3:17])([CH2:8][CH2:9][CH2:10][C:11]2([CH3:15])[CH3:16])[C@H:6]1[CH:5]=[O:18])=[O:19]

Participants

5

Reactant 2

HCID 69893717HCID 69893717, compoundHCID 178418268HCID 178418268, compound

Product 1

HCID 12990580HCID 12990580, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 0.30 g (1.1 mmol) of lactols 9S and 9R in 15 mL of benzene under argon was added 0.60 g (1.3 mmol) of lead tetraacetate. After the mixture was stirred at 25° C. for 4 h, it was diluted with diethyl ether, the organic layer was washed with water, and brine, dried (MgSO4), concentrated, and column chromatographed on silica gel using a gradient mixture of hexane and diethyl ether as eluent to give 0.25 g (85% yield) of aldehyde 11. [α]22D=−54.4° (c 0.25, CHCl3); 1H NMR (CDCl3) δ 9.98 (d, J=4Hz, 1H, CHO), 7.92 (s, 1H, OCHO), 2.55 (dd, J=9.6, 3.2Hz, 1H, C4a-H), 2.49 (d, J=4Hz, 1H, C1-H), 1.85 (s, 3H, Me), 1.84˜0.90 (m, 10H), 1.18 (s, 3H, Me), 0.89 (s, 3H, Me), 0.83 (s, 3H, Me); 13C NMR (CDCl3) δ 204.2 (C═O), 160.1 (C═O), 85.9, 68.9, 55.1, 41.7, 40.0, 39.9, 39.1, 33.4, 22.3, 21.6, 21.5, 20.0, 18.1, 17.2.

Workup

  1. washthe organic layer was washed with water, and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customcolumn chromatographed on silica gel using
  5. additiona gradient mixture of hexane and diethyl ether as eluent

Sources & evidence

ORD record
ord-73310c2b3a0d4c36b792ddc1985805f8
Source dataset
uspto-grants-2004_04
Patent number
US06727277B1

Reaction notes

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