Two syntheses of the 16- and 17-membered DEF ring systems of chloropeptin and complestatin.
[formula: see text] Two syntheses of a model system of the DEF ring system of complestatin and chloropeptin are described. The key step in both of these syntheses involves the formation of the biaryl linkage using a palladium-catalyzed Suzuki cross-coupling reaction and a catalytic enantioselective ene reaction to form the 6-bromo-D-tryptophan. Additionally, ring contraction of the 17-membered DEF ring system of complestatin generates the 16-membered DEF ring system of chloropeptin in a biomimetic fashion.
Elder
A M
AM
Department of Chemistry, University of Wisconsin, Madison 53706, USA.
Rich
D H
DH
D002733:Chlorophenols / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D010456:Peptides, Cyclic
D002733:Chlorophenols; D009842:Oligopeptides; D010456:Peptides, Cyclic; C090485:chloropeptin I; C023490:complestatin