Sodium borohydride → mycotrienol I

HRID 2186669Notes

Reaction equation

HRID 2186669 reaction equation
[CH3:1][C@H:2]1[C@@H:27]([OH:28])[C:26]([CH3:29])=[CH:25][CH2:24][CH2:23][C:18]2=[CH:19][C:20]([OH:22])=[CH:21][C:16](=[C:17]2[OH:30])[NH:15][C:13](=[O:14])[CH2:12][C@@H:11]([O:31][CH3:32])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=[CH:5][CH2:4][C@@H:3]1[O:33]C([C@H](NC(C1CCCCC1)=O)C)=O.[BH4-].[Na+]>C(Cl)Cl.CO>[CH3:1][C@@H:2]1[C@H:27]([OH:28])[C:26]([CH3:29])=[CH:25][CH2:24][CH2:23][C:18]2[C:17](=[O:30])[C:16](=[CH:21][C:20]([CH:19]=2)=[O:22])[NH:15][C:13](=[O:14])[CH2:12][C@@H:11]([O:31][CH3:32])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=[CH:5][CH2:4][C@H:3]1[OH:33]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 644088811050-90-1

Product 1

HCID 6440886mycotrienol IYield 84.4%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Mycotrienin II (1.00 g, 1.56 mmol) was reduced with NaBH4 as described by the literature method to afford 1.04 g of a crude material. The crude material was immediately oxidized with FeCl3 as described by the literature method to afford 600 mg of Mycotrienol I as a yellow solid after chromatography (25:1 CH2Cl2/methanol, Rf=0.44) in 87% combined yield.

Workup

  1. customto afford 1.04 g of a crude material

Sources & evidence

ORD record
ord-b77ba42502044ab8bb0f542cdd36d796
Source dataset
uspto-grants-2002_06
Patent number
US06407087B1

Reaction notes

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