Wortmannin → 17beta-Hydroxy wortmannin

HRID 1720095Notes

Reaction equation

HRID 1720095 reaction equation
[CH3:1][C:2]([O:4][C@H:5]1[C:14]2[C@@:15]3([CH3:30])[C@@H:26]([CH2:27][O:28][CH3:29])[O:25][C:23](=[O:24])[C:17]4=[CH:18][O:19][C:20]([C:21](=[O:22])[C:13]=2[C@@H:8]2[CH2:9][CH2:10][C:11](=[O:12])[C@@:7]2([CH3:31])[CH2:6]1)=[C:16]34)=[O:3].[H-].C([Al+]CC(C)C)C(C)C>C1COCC1.C1(C)C=CC=CC=1>[CH3:1][C:2]([O:4][C@H:5]1[C:14]2[C@:15]3([CH3:30])[C:16]4[C:17](=[CH:18][O:19][C:20]=4[C:21](=[O:22])[C:13]=2[C@@H:8]2[CH2:9][CH2:10][C@H:11]([OH:12])[C@@:7]2([CH3:31])[CH2:6]1)[C:23](=[O:24])[O:25][C@@H:26]3[CH2:27][O:28][CH3:29])=[O:3]

Participants

5

Reactant 2

HCID 312145WortmanninHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 986734017beta-Hydroxy wortmanninYield 70%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of wortmannin (100 mg) stirring in THF at -78° C. was added diisobutylaluminum hydride (0.4 mL of a 1.0M solution in toluene, 0.4 mmol). After 0.5 hour, the reaction was quenched with saturated aqueous NaHCO3. The mixture was then warmed to room temperature and extracted with CH2Cl2. The combined organic extracts were washed with brine and dried (MgSO4). The crude material was purified by radial chromatography (SiO2, 4 mm, 9:1 EtOAc/Hexanes) to give a 70% yield of 17β-hydroxywortmannin as an off-white powder.

Workup

  1. customthe reaction was quenched with saturated aqueous NaHCO3
  2. extractionextracted with CH2Cl2
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. customThe crude material was purified by radial chromatography (SiO2, 4 mm, 9:1 EtOAc/Hexanes)

Sources & evidence

ORD record
ord-b837b0b586744f85b1888a9fa7d48604
Source dataset
uspto-grants-1996_04
Patent number
US05504103

Reaction notes

Loading…