Synthesis of diastereomers of complestatin and chloropeptin I: substrate-dependent atropstereoselectivity of the intramolecular Suzuki-Miyaura reaction

Atropisomers as well as CC2 epimers of complestatin and chloropeptin I are readily synthesized through an intramol. SNAr reaction and the Suzuki-Miyaura reaction. The abs. configuration of amino acid N-methyl-2-(3,5-dichloro-4-hydroxyphenyl)glycine was found to det. the atropselectivity of the aryl-aryl bond-forming reaction. [on SciFinder (R)]


Published in:
Angewandte Chemie, International Edition, 47, 22, 4167-4172
Year:
2008
Keywords:
Note:
CAN 149:224538
34-3
Amino Acids, Peptides, and Proteins
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
1433-7851
written in English.
72287-26-4 Role: CAT (Catalyst use), USES (Uses) (total synthesis of diastereomers of complestatin and chloropeptin with atropstereoselective intramol. Suzuki-Miyaura reaction as a key step); 69598-75-0 (Complestatin); 160219-64-7 (Chloropeptin I) Role: MSC (Miscellaneous) (total synthesis of diastereomers of complestatin and chloropeptin with atropstereoselective intramol. Suzuki-Miyaura reaction as a key step); 1042907-15-2P Role: PRP (Properties), RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (total synthesis of diastereomers of complestatin and chloropeptin with atropstereoselective intramol. Suzuki-Miyaura reaction as a key step); 26973-43-3; 57591-61-4; 400778-04-3; 854443-88-2; 1042907-14-1; 1042907-16-3; 1042907-29-8; 1042907-31-2; 1042907-34-5; 1043894-16-1; 1143947-61-8 Role: RCT (Reactant), RACT (Reactant or reagent) (total synthesis of diastereomers of complestatin and chloropeptin with atropstereoselective intramol. Suzuki-Miyaura reaction as a key step); 586413-55-0P; 586413-73-2P; 854443-92-8P; 1042907-17-4P; 1042907-18-5P; 1042907-19-6P; 1042907-20-9P; 1042907-21-0P; 1042907-22-1P; 1042907-23-2P; 1042907-24-3P; 1042907-25-4P; 1042907-26-5P; 1042907-27-6P; 1042907-28-7P; 1042907-30-1P; 1042907-32-3P; 1042907-33-4P; 1042907-35-6P; 1043894-01-4P; 1043894-03-6P; 1043894-05-8P; 1043894-07-0P; 1043894-09-2P; 1043894-15-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (total synthesis of diastereomers of complestatin and chloropeptin with atropstereoselective intramol. Suzuki-Miyaura reaction as a key step); 854613-13-1P; 1043893-99-7P; 1043894-11-6P; 1043894-13-8P; 1043902-22-2P (Epi-AA-Cc2-complestatin methyl ester); 1043902-24-4P (Epi-AA-Cc2-isochloropeptin methyl ester) Role: SPN (Synthetic preparation), PREP (Preparation) (total synthesis of diastereomers of complestatin and chloropeptin with atropstereoselective intramol. Suzuki-Miyaura reaction as a key step)
Laboratories:




 Record created 2010-11-25, last modified 2018-09-13


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