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Chinese Journal of Organic Chemistry >

2015 , Vol. 35 >Issue 5: 1033 - 1039

DOI: https://doi.org/10.6023/cjoc201502029

ARTICLE

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

  • Xu Nanhui ,
  • Chen Heru
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  • 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 date: 2015-02-24

  Revised date: 2015-03-17

  Online published: 2015-03-24

Supported by

Project supported by the National Natural Science Foundation of China (No.81172982).

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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

Cite this article

Xu Nanhui , Chen Heru . An Efficient Total Synthesis of Ethyl 7-(Hydroxyimino)cyclopropa-[b]chromen-1a-carboxylate and Their Derivatives[J]. Chinese Journal of Organic Chemistry, 2015 , 35(5) : 1033 -1039 . DOI: 10.6023/cjoc201502029

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