Total synthesis of tetracyclic kynurenic acid analogues isolated from chestnut honey

TETRAHEDRON LETTERS

卷:59

Article

Cincinelli, Raffaella¹  Beretta, Giangiacomo²  Dallavalle, Sabrina¹ 

[1] Univ Milan, Dept Food Environm & Nutr Sci, Div Chem & Mol Biol, Via Celoria 2, I-20133 Milan, Italy

[2] Univ Milan, Dept Environm Sci & Policy ESP, Via Mangiagalli 25, I-20133 Milan, Italy

关键词: Kynurenic acid analogues;    Chestnut honey;    Natural products;    Microwave assisted synthesis;   

DOI  :  10.1016/j.tetlet.2017.12.015

来源: Elsevier

【 摘 要 】

A short and efficient synthesis of novel tetracyclic Kynurenic acid analogues, isolated from chestnut honey, is described. The crucial step of the strategy was a MW-assisted cyclization of enamines of ethyl dioxohexahydropyrrolizine and 2,3-dioxooctahydroindolizine carboxylates to obtain 2,3,6,11b-tetrahydro-1H-pyrrolizino[2,1-b]quinoline-5,11-dione and 5,8,91,011,11a-hexahydroindolizino[2,1-b]quinoline-6,12-dione, respectively. Because of its modular nature, the synthetic strategy can have value as a general method for the preparation of compounds containing these new heterocyclic scaffolds. (C) 2017 Elsevier Ltd. All rights reserved.

【 授权许可】

Free