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Synthesis 2010(19): 3325-3331  
DOI: 10.1055/s-0030-1258187
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Formal Total Synthesis of Fostriecin by a Convergent Approach

Deyao Lia, Yu Zhaoa, Liu Yea, Chaonan Chena, Jiancun Zhang*a,b
a Guangzhou Institutes of Biomedicine and Health, CAS, 190 Kaiyuan Avenue, Science Park, Guangzhou 510530, P. R. of China
b State Key Laboratory of Respiratory Diseases, Guangzhou Medical College, Guangzhou 510120, P. R. of China
Fax: +86(20)32015323; e-Mail: Zhang_jiancun@gibh.ac.cn;
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Publication History

Received 30 April 2010
Publication Date:
16 July 2010 (online)

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Abstract

A formal total synthesis of fostriecin has been accomplished in 20 steps. Our method features the derivation of two of the four chiral centers from commercial diethyl d-(+)-malate. The key steps involve the Julia-Kocienski olefination, the Sharpless asymmetric dihydroxylation, and the Stille coupling.

Key words

fostriecin - chiral pool - Julia-Kocienski olefination - Sharpless asymmetric dihydroxylation - Stille coupling

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