Carbon Dioxide → 1,1a,2,8,8a,8b-Hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methyl-6-(allyloxy)-azirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione carbamate

Participants

Reaction Steps

A solution of mitomycin A (100 mg or 0.286 mmole) in 4 ml of allyl alcohol was stirred at room temperature and under nitrogen for 45 minutes with 500 mg of a 1.6% solution of potassium hydroxide (KOH) in allyl alcohol. The reaction mixture was decomposed with excess dry ice while immersing the flask into a water bath at room temperature. It was then isolated on a silica gel plate using ether, which elutes the allyl alcohol to the top of the plate (the plate was developed several times), followed by CHCl3 -acetone 1:1 which elutes the product. This procedure gives 45 mg (42%) of the title compound, having a melting point of 106°-111° C. (decomposition) and providing the following analysis:

Provenance & Evidence