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Synthesis of circumdatin F and sclerotigenin. Use of the 2-nitrobenzyl group for protection of a diketopiperazine amide; synthesis of ent -fumiquinazoline G
Journal article   Peer reviewed

Synthesis of circumdatin F and sclerotigenin. Use of the 2-nitrobenzyl group for protection of a diketopiperazine amide; synthesis of ent -fumiquinazoline G

Barry B Snider and Marina V Busuyek
Tetrahedron, Vol.57(16), pp.3301-3307
04/16/2001
DOI: https://doi.org/10.1016/S0040-4020(01)00208-3

Abstract

aza Wittig reaction alkaloids protecting groups Chemical Synthesis Organic Chemistry Photochemistry
The Eguchi aza Wittig protocol has been used for the synthesis of sclerotigenin and circumdatin F by selective acylation of the more acidic anilide nitrogen of a benzodiazepinedione without the need for protecting groups. The use of the 2-nitrobenzyl group as a photochemically labile protecting group for the amide nitrogen of a diketopiperazine permits the use of the aza Wittig procedure for the synthesis of fumiquinazoline G.

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