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Synthesis 2006(15): 2535-2542  
DOI: 10.1055/s-2006-942467
PAPER
© Georg Thieme Verlag Stuttgart · New York

Stereocontrolled Synthesis of gem-Difluoromethylenated Goniodiols and Goniothalamin Epoxides Based on Ring-Closing Metathesis

Zheng-Wei Youa, Xingang Zhanga, Feng-Ling Qinga,b
a Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 354 Fenglin Lu, Shanghai 200032, P. R. of China
b Institute of Biological Sciences and Biotechnology, Donghua University, 2999 North Renmin Lu, Shanghai 201620, P. R. of China
Fax: +86(21)64166128; e-Mail: flq@mail.sioc.ac.cn;
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Publication History

Received 27 February 2006
Publication Date:
04 July 2006 (online)

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Abstract

An efficient and general method to stereoselectively synthesize gem-difluoromethylenated goniodiols and goniothalamin epoxides has been developed. The introduction of a gem-difluoro­methyl-containing group was achieved by the reaction of aldehydes with 3-bromo-3,3-difluoropropene in the presence of indium. The gem-difluoromethylenated α,β-unsaturated-δ-lactone moiety was constructed through the ring-closing metathesis of highly electron-deficient gem-difluoromethylenated acryloyl esters by Grubbs’ II catalyst in toluene at reflux.

Key words

gem-difluoromethylenated compounds - styryllactone - ring-closing metathesis - α,β-unsaturated-δ-lactone