Water → HCID 101616408, compound
Reaction equation
CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].[CH3:15][C@H:16]1[C@@:30]([C:32]2[C:36]3[CH:37]=[CH:38][C:39]([OH:41])=[CH:40][C:35]=3[NH:34][CH:33]=2)([CH3:31])[C@@H:29]2[C@:19]([CH3:44])([C@H:20]3[C@:26]([CH3:42])([CH2:27][CH2:28]2)[C@@H:25]([CH3:43])[C:23](=[O:24])[CH2:22][CH2:21]3)[CH2:18][CH2:17]1.O.S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1.C(Cl)Cl>[CH3:15][C@H:16]1[C@@:30]([C:32]2[C:36]3[CH:37]=[CH:38][C:39]([OH:41])=[CH:40][C:35]=3[NH:34][CH:33]=2)([CH3:31])[C@@H:29]2[C@:19]([CH3:44])([C@H:20]3[C@:26]([CH3:42])([CH2:27][CH2:28]2)[C@@H:25]([CH3:43])[C@@H:23]([OH:24])[CH2:22][CH2:21]3)[CH2:18][CH2:17]1Participants
7
Conditions
- Temperature
- -78 °C
Procedure
L-Selectride (45 μl of a 1.0M solution in tetrahydrofuran) was added to a 2-ml reaction vial at -78° C. containing 2.0 mg of radarin A in 1.0 ml of dry tetrahydrofuran. After the mixture was stirred for 30 min at -78° C., water (50 μl) was added and the mixture was allowed to warm to room temperature (15 min). Anhydrous magnesium sulfate was added and the solution was then passed through a small silica column. The product obtained upon evaporation of the solvent was redissolved in 1.0 ml methylene chloride and extracted with water (5×1 ml). The organic phase was dried and evaporated to yield radarin B (1.9 mg, 95% yield) which was identical to the natural product based on 1H NMR and HPLC analysis.
Workup
- temperatureto warm to room temperature (15 min)
- customThe product obtained upon evaporation of the solvent
- extractionextracted with water (5×1 ml)
- customThe organic phase was dried
- customevaporated
Sources & evidence
- ORD record
- ord-a7567838c570400aa098d75c7f8bf8d5
- Source dataset
- uspto-grants-1992_04
- Patent number
- US05106865
Reaction notes
Loading…