Synthesis of Spongidepsin and Analogs
Dr. Laurent Ferrié
BioCIS, Faculté de Pharmacie, Université Paris-Saclay, 5 rue J. B. Clément, 92290 Châtenay-Malabry, France
Search for more papers by this authorOndine Picot
Molecular, Macromolecular Chemistry and Materials, ESPCI Paris, PSL University, CNRS, 75005 Paris, France
Search for more papers by this authorDr. Amandine Guérinot
Molecular, Macromolecular Chemistry and Materials, ESPCI Paris, PSL University, CNRS, 75005 Paris, France
Search for more papers by this authorCorresponding Author
Prof. Janine Cossy
Molecular, Macromolecular Chemistry and Materials, ESPCI Paris, PSL University, CNRS, 75005 Paris, France
Molecular, Macromolecular Chemistry and Materials, ESPCI Paris, PSL University, CNRS, 75005 Paris, France
E-mail: [email protected]
https://www.lco.espci.fr/-Prof-Janine-Cossy-
Search for more papers by this authorDr. Laurent Ferrié
BioCIS, Faculté de Pharmacie, Université Paris-Saclay, 5 rue J. B. Clément, 92290 Châtenay-Malabry, France
Search for more papers by this authorOndine Picot
Molecular, Macromolecular Chemistry and Materials, ESPCI Paris, PSL University, CNRS, 75005 Paris, France
Search for more papers by this authorDr. Amandine Guérinot
Molecular, Macromolecular Chemistry and Materials, ESPCI Paris, PSL University, CNRS, 75005 Paris, France
Search for more papers by this authorCorresponding Author
Prof. Janine Cossy
Molecular, Macromolecular Chemistry and Materials, ESPCI Paris, PSL University, CNRS, 75005 Paris, France
Molecular, Macromolecular Chemistry and Materials, ESPCI Paris, PSL University, CNRS, 75005 Paris, France
E-mail: [email protected]
https://www.lco.espci.fr/-Prof-Janine-Cossy-
Search for more papers by this authorGraphical Abstract
Spongidepsin is a macrolide isolated from Spongia sp. Owing to its original structure, exhibiting a phenylalanine amino acid moiety in a macrocycle and the presence of a terminal alkyne, associated to its antiproliferative activity, the molecule has attracted synthetic chemists culminating in seven total and/or formal syntheses. The major differences in the syntheses rely on the methods used to synthesize the C1–C5, the C6–C11, or C6–13 fragments as their connectivities to access spongidepsin are similar. The different methods to synthesize spongidepsin are compared.
Abstract
Seven syntheses of (–)-spongidepsin, a natural product isolated from Spongia sp. with moderate antiproliferative activity, are described and the different analogs obtained during these syntheses are reported. A comparison between the different syntheses has been achieved.
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