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The antitumor antibiotics FR66979 and FR900482 are believed to undergo bioreductive activation in vivo, enabling them to alkylate DNA. Reduction has previously been accomplished in vitro using sodium dithionite or dithiothreitol. We find that metal ions are a previously unrecognized, critical component of these reactions, which are suppressed by addition of EDTA and greatly stimulated by addition...
An efficient (21% overall yield), enantio- and diastereoselective, 11-step synthesis of (1S,2R)-imidazoleglycerol has been developed. The key steps are the stereoselective hydroxylation of an acyloxazolidinone enolate, the alkylation of a thioester with (MOMOCH 2 ) 2 CuLi and the stereodivergent reduction of the resulting ketone. The scope of the reaction of the enolate derived from...
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