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, b, Zhou Caob, Chengzhong Sub, Zefeng Chenc, Xianran Hea, b, Fei Dinga, b, Hang Lia, b, Yongmin Zhang*a, d
  • aInstitute for Interdisciplinary Research, Jianghan University, Wuhan Economic and Technological Development Zone, Wuhan 430056, P. R. of China   Email: sunlt413@jhun.edu.cn
  • bKey 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
  • cChimie, IUT d’Orsay, Université Paris Sud, Plateau de Moulon, 91400 Orsay, France
  • dInstitut 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
Further Information

Publication History

Received: 10 August 2016

Accepted after revision: 17 October 2016

Publication Date:
18 November 2016 (eFirst)

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.

Supporting Information