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Synlett 2011(19): 2779-2788  
DOI: 10.1055/s-0031-1289862
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© Georg Thieme Verlag Stuttgart ˙ New York

Various Entries to Vinyl Chloride Derivatives and their Applications in Total Synthesis of Natural Products

Xavier Guinchard, Emmanuel Roulland*
CNRS, Institut de Chimie des Substances Naturelles, Centre de Recherche de Gif, 91198 Gif-sur-Yvette, Cedex, France
Fax: +33(1)69827247; e-Mail: emmanuel.roulland@icsn.cnrs-gif.fr;
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Publication History

Received 7 June 2011
Publication Date:
09 November 2011 (online)

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Abstract

Our program of total synthesis of natural products stimulated our imagination and led us to design various methodologies to build the vinyl chloride function of our targets. The access to vinyl chlorides also offers an entry to the trisubstituted alkenes of pure configuration. Thanks to these methodologies we achieved the synthesis of complex structures such as (+)-oocydin A, a total synthesis that also led us to discover other useful new transformations.

1 Introduction

1.1 Natural Products Containing a Vinyl Chloride Function

1.2 Known Accesses to Vinyl Chlorides Using Organometallic Catalysis

2 Our Methods for the Synthesis of (Z)-vinyl chlorides

2.1 Palladium-Catalyzed Cross-Coupling of 1,1-Dichloro-1-alkenes with Alkyl-9-BBN

2.2 Palladium-Catalyzed Carbonylation of 1,1-Dichloro-1-­alkenes

2.3 Study of the Behavior of Potassium (Z)-2-Chloroalk-1-enyl Trifluoroborates in Pd-Catalyzed Reactions

2.3.1 Synthesis of Potassium (Z)-2-Chloroalk-1-enyltrifluoro­borate Derivatives

2.3.2 Searching for Chemoselective Cross-Coupling Conditions

3 Applications of Our Methodologies

3.1 Total Synthesis of Oocydin A

3.2 Stereoselective Syntheses of Trisubstituted Alkenes

3.3 Total Synthesis of an N-Acyl Spermidine

4 Concluding Remarks and Future Outlook

Key words

total synthesis - natural products - palladium - cross-­coupling - boron - trifluoroborates - carbon monoxide

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Performed by the IMAGIF platform in Gif-sur-Yvette (https://www.imagif.cnrs.fr).