Journal of Organic Chemistry p. 1879 - 1884 (1985)
Update date:2022-08-05
Topics:
Nair, M. G.
Methods have been developed for the chemical synthesis of two recently described potent antitumor agents.They are 10-deazaaminopterin (10-DAAM) (2) and 10-ethyl-10-deazaaminopterin (10-EDAAM) (3).The methods described in this paper have general applicability for the synthesis of a variety of hitherto difficulty accessible 10-substituted-10-deazafolic acids and analogues.Reaction of methyl p-formylbenzoate (7) with the Wittig reagent 6 derived from N-(3-bromo-2-oxopropyl)phtalimide (5) and triphenylphosphine gave the common intermediate 8, which was used for the synthesis of both 2 and 3.This enone was reduced with Zn/HOAc to 15 and was used for the synthesis of 2.Alternately 8 was reacted with ethylmagnesium bromide in the presence of cuprous bromide to obtain the conjugate addition product 16.Both 15 and 16 were converted to the masked α-amino ketones 20 and 21 reacted with 6-chloro-2,4-diamino-5-nitropyrimidine to obtain 22 and 23.These pyrimidine intermediates were subsequently elaborated to the pteroic acid analogues 26 and 27 by multistep procedures previously described from this laboratory.The target compounds 2 and 3 were prepared from 26 and 27 by standard coupling procedures involving isobutyl chloroformate and diethyl L-glutamate.
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Doi:10.1246/cl.1985.195
(1985)Doi:10.1055/s-1984-31046
(1984)Doi:10.1021/jo01066a054
(1961)Doi:10.1016/S0040-4020(01)83488-8
(1985)Doi:10.1021/jm00147a040
(1985)Doi:10.1021/jo00213a033
(1985)