Dihydroxylation of 9,10-Dihydrobenzo[h]coumarins and Synthesis of Their Ester Derivatives

Chin. J. Org. Chem. ›› 2010, Vol. 30 ›› Issue (05): 726-730. Previous Articles Next Articles

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9,10-二氢苯并[h]香豆素类化合物的双羟化反应研究及酯化产物的合成

王洁¹，夏鹏*^{,1，王洋*^,1,2}

(¹复旦大学药学院药物化学教研室上海 201203)
(²中国科学院上海药物研究所新药研究国家重点实验室上海 201203)

收稿日期:2010-02-26 修回日期:2010-03-29 发布日期:2010-04-07
通讯作者: 王洋 E-mail:wangyang@shmu.edu.cn
基金资助:
国家自然科学基金

Dihydroxylation of 9,10-Dihydrobenzo[h]coumarins and Synthesis of Their Ester Derivatives

Wang Jie¹ Xia Peng*^{,1 Wang Yang*^,1,2}

(¹ Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai 201203)
(² State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203)

Received:2010-02-26 Revised:2010-03-29 Published:2010-04-07
Contact: Yang WANG E-mail:wangyang@shmu.edu.cn

Abstract

The asymmetric dihydroxylation of 9,10-dihydrobenzo[h]coumarins (1a, 1b) provided not only enantiomerically enriched cis-7,8-diols (2a, 2b) but also 7-keto-8-hydroxy compounds 3a, 3b which were obtained in moderate yields (52% and 45%, respectively) by the overoxidation of the corresponding diols. The influence of the amount of oxidant and the reaction temperature on the distribution of products were discussed and the ee values of the diols 2a, 2b were deduced approximately from the diasteromeric ratios of their corresponding camphanoyl esters (4a, 4b) by ¹H NMR spectra. The structures of overoxidation product 3b and its camphanoyl ester 5b were determined by X-ray diffraction analysis.

Key words: 9,10-dihydrobenzo[h]coumarin, dihydroxylation, overoxidation, camphanoyl ester

Cite this article

WANG Jie, XIA Peng, WANG Yang. Dihydroxylation of 9,10-Dihydrobenzo[h]coumarins and Synthesis of Their Ester Derivatives[J]. Chin. J. Org. Chem., 2010, 30(05): 726-730.

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9,10-二氢苯并[h]香豆素类化合物的双羟化反应研究及酯化产物的合成

Dihydroxylation of 9,10-Dihydrobenzo[h]coumarins and Synthesis of Their Ester Derivatives

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