The Synthesis of the Optically Active Ethyl Polyhydroxy Heptanoate

Acta Chimica Sinica ›› 2007, Vol. 65 ›› Issue (1): 32-36. Previous Articles Next Articles

Original Articles

光学活性化合物多羟基庚酸乙酯的合成

王进欣¹,2, 何玲¹, 尤启冬*^,1, 李灜*^,2

(¹中国药科大学药学院南京 210009)
(²兰州大学功能有机分子化学国家重点实验室兰州 730000)

投稿日期:2006-03-08 修回日期:2006-04-10 发布日期:2007-01-14
通讯作者: 尤启冬

The Synthesis of the Optically Active Ethyl Polyhydroxy Heptanoate

WANG Jin-Xin¹,2; HE Ling¹; YOU Qi-Dong*^,1; LI Ying*^,2

(¹School of Pharmacy, China Pharmaceutical University, Nanjing 210009)
(² State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000)

Received:2006-03-08 Revised:2006-04-10 Published:2007-01-14

Abstract

The first synthesis of ethyl (＋)-(2R,3S,4S,5S)-4,5-epoxy-2,3-dihydroxy-6-methyl heptanoate (5) and ethyl (－)-(2R,3S,4R,5S)-2,3,4,5-tetrahydroxy-6-methyl heptanoate (11) was achieved and the key steps involved the construction of chiral carbon centers by the asymmetric epoxidation and dihydroxylation. This efficiently concise strategy has better stereochemistry and is adapted to the synthesis of polyhydroxyl fatty acid analogues. The primary tests of compounds 5 and 11 showed better inhibitory activities against HL60 cell line.

Key words: (＋)-(2R,3S,4S,5S)-4,5-epoxy-2,3-dihydroxy-6-methyl heptanoate, ethyl (－)-(2R,3S,4R, 5S)-2,3,4,5-tetrahydroxy-6-methyl heptanoate, asymmetric dihydroxylation, antitumor activity

Cite this article

WANG Jin-Xin^1,2; HE Ling; YOU Qi-Dong*^,1; LI Ying*^,2. The Synthesis of the Optically Active Ethyl Polyhydroxy Heptanoate[J]. Acta Chimica Sinica, 2007, 65(1): 32-36.

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光学活性化合物多羟基庚酸乙酯的合成

The Synthesis of the Optically Active Ethyl Polyhydroxy Heptanoate

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