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Synthesis 2011(23): 3807-3814  
DOI: 10.1055/s-0031-1289293
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient Synthesis of Novel Jolkinolides and Related Derivatives Starting from Stevioside

Lian-Yong Shia, Jia-Qiang Wua, Da-Yong Zhang*a, Yang-Chang Wub, Wei-Yi Huaa, Xiao-Ming Wu*a
a Center of Drug Discovery, College of Pharmacy, China Pharmaceutical University, 24 Tongjia Xiang Road, Nanjing 210009, P. R. of China
Fax: +86(25)83271307; e-Mail: zhangdayong@cpu.edu.cn; e-Mail: xmwu@cpu.edu.cn;
b Graduate Institute of Pharmaceutical Chemistry, College of Pharmacy, China Medical University, 91 Hsueh-Shih Road, Taichung 40402, Taiwan
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Publication History

Received 11 July 2011
Publication Date:
20 October 2011 (online)

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Abstract

Jolkinolides are naturally occurring tetracyclic diterpene from Euphorbia genus, which exhibit promising antitumor and other biological activity. Efficient syntheses of the 19-carboxy derivative of jolkinolide A and 19-hydroxyjolkinolide E have been accomplished in 13 steps with a total yield of 7.8% starting from the easily available and low-cost sweetener stevioside, and some related derivatives have also been synthesized.

Key words

jolkinolides - Euphorbiaceae - stevioside - antitumor