The Journal of Organic Chemistry

A new approach to the synthesis of the CC-1065/duocarmycin pharmacophore

JH Tidwell, SL Buchwald

Index: Tidwell, Jeffrey H.; Buchwald, Stephen L. Journal of Organic Chemistry, 1992 , vol. 57, # 24 p. 6380 - 6382

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Citation Number: 31

Abstract

The symmetrical bis-cholestanyl pyrazine was also prepared as shown in Scheme II. Thus, treatment of azido ketone 3 with 0-met. hylhydroxy1amine provided the 0-methyloxime, which was reduced with triphenylphosphine in aqueous THF to obtain the 2-amino-3-oxime derivative of cholestane 5. This material was heated in toluene at 140 OC to obtain pyrazine 4 in about 77% overall yield from 3.