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Synthesis 2016; 48(24): 4471-4476
DOI: 10.1055/s-0036-1588343
paper
© Georg Thieme Verlag Stuttgart · New York

Chiron Approaches to the Antitumor Natural Product Fuzanin D

Yangguang Gao*
a   Institute for Interdisciplinary Research, Jianghan University, Wuhan Economic and Technological Development Zone, Wuhan 430056, P. R. of China   eMail: sunlt413@jhun.edu.cn
b   Key Laboratory of Optoelectronic Chemical Materials and Devices of Ministry of Education, Jianghan University, Wuhan Economic and Technological Development Zone, Wuhan 430056, P. R. of China
,
Zhou Cao
b   Key Laboratory of Optoelectronic Chemical Materials and Devices of Ministry of Education, Jianghan University, Wuhan Economic and Technological Development Zone, Wuhan 430056, P. R. of China
,
Chengzhong Su
b   Key Laboratory of Optoelectronic Chemical Materials and Devices of Ministry of Education, Jianghan University, Wuhan Economic and Technological Development Zone, Wuhan 430056, P. R. of China
,
Zefeng Chen
c   Chimie, IUT d’Orsay, Université Paris Sud, Plateau de Moulon, 91400 Orsay, France
,
Xianran He
a   Institute for Interdisciplinary Research, Jianghan University, Wuhan Economic and Technological Development Zone, Wuhan 430056, P. R. of China   eMail: sunlt413@jhun.edu.cn
b   Key Laboratory of Optoelectronic Chemical Materials and Devices of Ministry of Education, Jianghan University, Wuhan Economic and Technological Development Zone, Wuhan 430056, P. R. of China
,
Fei Ding
a   Institute for Interdisciplinary Research, Jianghan University, Wuhan Economic and Technological Development Zone, Wuhan 430056, P. R. of China   eMail: sunlt413@jhun.edu.cn
b   Key Laboratory of Optoelectronic Chemical Materials and Devices of Ministry of Education, Jianghan University, Wuhan Economic and Technological Development Zone, Wuhan 430056, P. R. of China
,
Hang Li
a   Institute for Interdisciplinary Research, Jianghan University, Wuhan Economic and Technological Development Zone, Wuhan 430056, P. R. of China   eMail: sunlt413@jhun.edu.cn
b   Key Laboratory of Optoelectronic Chemical Materials and Devices of Ministry of Education, Jianghan University, Wuhan Economic and Technological Development Zone, Wuhan 430056, P. R. of China
,
Yongmin Zhang*
a   Institute for Interdisciplinary Research, Jianghan University, Wuhan Economic and Technological Development Zone, Wuhan 430056, P. R. of China   eMail: sunlt413@jhun.edu.cn
d   Institut Parisien de Chimie Moléculaire, CNRS UMR 8232, Université Pierre et Marie Curie-Paris 6, 4 place Jussieu, 75005 Paris, France   eMail: yongmin.zhang@upmc.fr
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Weitere Informationen

Publikationsverlauf

Received: 10. August 2016

Accepted after revision: 17. Oktober 2016

Publikationsdatum:
18. November 2016 (online)

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Abstract

Fuzanin D, a pyridine-containing natural product, which exhibits cytotoxic activity against DLD-1 cells, is synthesized in a concise manner using l-arabinose or ethyl l-lactate as chiral pool substrates in nine steps (14.4% overall yield) and six steps (30.8% overall yield), respectively. The key steps involve Wittig olefination and olefin cross-­metathesis.

Key words

synthesis - chiral pool - antitumor - cross-metathesis - olefination

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588343.
  • Supporting Information
 

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