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Synthesis 2010(2): 267-275  
DOI: 10.1055/s-0029-1217099
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Total Synthesis of gem-Difluoromethylenated Analogues of Pironetin

Jing Lina, Xuyi Yueb, Peng Huangc, Daxiang Cuic, Feng-Ling Qing*a,b
a College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, 2999 North Renmin Lu, Shanghai 201620, P. R. of China
b Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. of China
Fax: +86(21)64166128; e-Mail: flq@mail.sioc.ac.cn;
c Institute of Micro-Nano Science and Technology, Shanghai Jiao Tong University, 800 Dongchuan Lu, Shanghai 200240, P. R. of China
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Publikationsverlauf

Received 17 August 2009
Publikationsdatum:
03. November 2009 (online)

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Abstract

The straightforward synthesis of four gem-difluoromethylenated analogues of pironetin is described. Our synthesis features the efficient construction of the key intermediates through the indium­-mediated gem-difluoropropargylation of aldehydes with the fluorine-containing building block.

Key words

pironetin - α,β-unsaturated δ-lactones - gem-difluoro­methylenated analogues