An Efficient Total Synthesis of Ethyl 7-(Hydroxyimino)cyclopropa-[b]chromen-1a-carboxylate and Their Derivatives

doi:10.6023/cjoc201502029

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (5): 1033-1039.DOI: 10.6023/cjoc201502029 Previous Articles Next Articles

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(1aRS,7aRS)-7-羟基氨亚基-1,1a,7,7a-4H-丙环骈[b]色烯-1a-甲酸乙酯及其衍生物的有效全合成

许男徽^a, 陈河如^a,b

a 暨南大学药学院中药及天然药物研究所广州 510632;
b 广东省中药药效物质基础及创新药物研究重点实验室广州 510632

收稿日期:2015-02-24 修回日期:2015-03-17 发布日期:2015-03-24
通讯作者: 陈河如 E-mail:thrchen@jnu.edu.cn
基金资助:
国家自然科学基金(No.81172982)资助项目.

An Efficient Total Synthesis of Ethyl 7-(Hydroxyimino)cyclopropa-[b]chromen-1a-carboxylate and Their Derivatives

Xu Nanhui^a, Chen Heru^a,b

a Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632;
b Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine and New Drugs Research, Jinan University, Guangzhou 510632

Received:2015-02-24 Revised:2015-03-17 Published:2015-03-24
Supported by:
Project supported by the National Natural Science Foundation of China (No.81172982).

1. An Efficient Total Synthesis of Ethyl 7-(Hydroxyimino)cyclopropa-[b]chromen-1a-carboxylate and Their Derivatives.PDF(2302KB)

Abstract

Ethyl 7-(hydroxyimino)cyclopropa[b]chromen-1a-carboxylate and their derivatives have been synthesized through directed acylation, intramolecular cyclization under the catalysis of iodine, cyclopropanation, esterification and oximation by using phenol and maleic anhydride as starting materials. In the current invetigation, the construction of chromone scaffold was improved and the cyclopropanation upon the treatment of Corey's dimethyloxosulfonium methylide was applied. The structures of all the intermediates and final products were confirmed by ¹H NMR, ¹³C NMR, and MS, respectively. The overall yields of these 5-step procedures were 20.1%~29.5%.

Key words: mGluR modulators, total synthesis, iodonium, cyclopropanation

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Xu Nanhui, Chen Heru. An Efficient Total Synthesis of Ethyl 7-(Hydroxyimino)cyclopropa-[b]chromen-1a-carboxylate and Their Derivatives[J]. Chin. J. Org. Chem., 2015, 35(5): 1033-1039.

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(1aRS,7aRS)-7-羟基氨亚基-1,1a,7,7a-4H-丙环骈[b]色烯-1a-甲酸乙酯及其衍生物的有效全合成

An Efficient Total Synthesis of Ethyl 7-(Hydroxyimino)cyclopropa-[b]chromen-1a-carboxylate and Their Derivatives

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