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DOI: 10.1055/s-0031-1289862
Various Entries to Vinyl Chloride Derivatives and their Applications in Total Synthesis of Natural Products
Publication History
Publication Date:
09 November 2011 (online)
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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References and Notes
Performed by the IMAGIF platform in Gif-sur-Yvette (https://www.imagif.cnrs.fr).