Total synthesis of complestatin (Chloropeptin II)

Complestatin was isolated in 1980 from the mycelium of Streptomyces lavendulae as inhibitor of alternative pathways to the complement cascade. An efficient synthesis of complestatin was developed. Intramol. Suzuki-Miyaura and SNAr reactions were employed for the construction of two macrocycles by the formation of aryl-aryl and aryl-aryl ether bonds, resp. A [3+3] segment coupling was used for the construction of the hexapeptide backbone, which makes this synthesis highly convergent. [on SciFinder (R)]


Published in:
Angewandte Chemie, International Edition, 49, 11, 2018-2022, S2018/1-S2018/23
Year:
2010
Keywords:
Note:
CAN 152:548318, 34-3, Amino Acids, Peptides, and Proteins, Centre de Recherche de Gif,Institut de Chimie des Substances Naturelles, CNRS,Gif-sur-Yvette,Fr., Journal, 1433-7851, written in English., 26973-43-3; 854443-88-2; 943975-88-0; 1225383-21-0; 1226519-37-4 Role: RCT (Reactant), RACT (Reactant or reagent) (total synthesis of complestatin (chloropeptin II) by segment coupling for backbone construction and by regioselective macrocyclization via Suzuki-Miyaura reaction and SNAr); 1225383-16-3P; 1225383-17-4P; 1225383-18-5P; 1225383-19-6P; 1225383-20-9P; 1226519-18-1P; 1226519-24-9P; 1226519-27-2P; 1226519-30-7P; 1226519-32-9P; 1226519-34-1P; 1226519-40-9P; 1226519-42-1P; 1226519-45-4P (Complestatin methyl ester) Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (total synthesis of complestatin (chloropeptin II) by segment coupling for backbone construction and by regioselective macrocyclization via Suzuki-Miyaura reaction and SNAr); 69598-75-0P (Complestatin); 1225383-22-1P; 1226519-21-6P; 1226519-39-6P Role: SPN (Synthetic preparation), PREP (Preparation) (total synthesis of complestatin (chloropeptin II) by segment coupling for backbone construction and by regioselective macrocyclization via Suzuki-Miyaura reaction and SNAr)
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 Record created 2010-11-25, last modified 2018-09-13


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