Borane → 17beta-Hydroxy wortmannin

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

For instance, as depicted in FIG. 4, a solution of 60 mg wortmannin (0.14 mmol from Aldrich) in 12 mL tetrahydrofuran (THF) is cooled in a 0° C. ice bath under nitrogen. 1M borane in THF solution (134 μL, 0.14 mmol from Aldrich) is added and the reaction mixture is stirred at 0° C. for 3.5 hours. The reaction is quenched with 1 mL water. After warming to room temperature, the reaction mixture is diluted with water and extracted with ethyl acetate. After work up, about 60 mg (90% pure 17-hydroxy-wortmannin by HPLC) solid is obtained. This solid (about 0.126 mmol 17-hydroxy-wortmannin) is dissolved in 15 mL methylene chloride, reacted with iodoacetic acid (24 mg, 0.13 mmol), dicyclohexylcarbodiimide (DCC) (27 mg, 0.13 mmol) and 4-N,N-dimethylaminopyridine (DMAP) (0.1 mg as catalyst). The reaction mixture is kept at room temperature for 1 hour. After work up, about 75 mg crude product (yellow solid) is obtained. Pure 17-dihydro-17-(1-iodoacetyl)-wortmannin is isolated by preparative HPLC. A total of 54 mg of white solid is obtained.

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