Boron trifluoride etherate → 17-Ethyl-1-hydroxy-12-[2'-(4"-hydroxy-3"-isopropoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone

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Reaction Steps

To a solution of 17-ethyl-1-hydroxy-12-[2'-(4",3"-dihydroxyoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo-[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (200 mg) in diethyl ether (6 ml) is added boron trifluoride etherate (10 ml) followed by freshly prepared 2-diazopropane (100-fold excess). The mixture is stirred at room temperature for 15 min. and quenched with sat'd aqueous sodium bicarbonate solution. The organic layer is separated, washed with sat's NaCl and dried over sodium sulfate. Removal of solvent followed by preparative TLC on silica gives the title compound and its 4" isomer.

Provenance & Evidence