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Paper | Regular issue | Vol 27, No. 8, 1988, pp.1925-1928
Published online, 1st January, 1970
DOI: 10.3987/COM-88-4597
■ Diels-Alder Reactions of 6-Azapterins. An Alternative Strategy for the Synthesis of 5,10-Dideaza-5,6,7,8-tetrahydrofolic Acid (DDATHF)

Edward C. Taylor,* Philip M. Harrington, and John C. Warner

*Department of Chemistry, Princeton University , Princeton, New Jersey 08544, U.S.A.

Abstract

Methyl 2-N-pivaloyl-5,10-dideazapteroate (7), a key intermediate in our recent unambiguous synthesis of the new antitumor agent, 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF), has been synthesized by a novel inverse electron demand Diels-Alder reaction between 2-N-pivaloyl-7-methylthio-6-azapterin (4) and the pyrrolidine enamine of methyl p-(4-oxobutyl) benzoate, followed by Raney nickel desulfurization of the resulting 7-methylthio derivative (5).