Synthesis of DEFG ring of complestatin and chloropeptin I: highly atropdiastereoselective macrocyclization by intramolecular Suzuki-Miyaura reaction
2007
Abstract
Palladium-catalyzed intramol. Suzuki-Miyaura reaction of linear tripeptide afforded the 16-membered DEFG ring of complestatin I in good yield with an excellent atropdiastereoselectivity. Acidic treatment of I triggers a stereospecific rearrangement leading to the corresponding DEFG ring II of chloropeptin I. [on SciFinder (R)]
Details
Title
Synthesis of DEFG ring of complestatin and chloropeptin I: highly atropdiastereoselective macrocyclization by intramolecular Suzuki-Miyaura reaction
Author(s)
Jia, Yanxing ; Bois-Choussy, Michele ; Zhu, Jieping
Published in
Organic Letters
Volume
9
Issue
12
Pages
2401-2404
Date
2007
ISSN
1523-7060
Keywords
Suzuki coupling reaction (intramol.; stereoselective prepn. of fragments of complestatin and chloropeptin I starting from nitroaniline and dihydroxy(iodo)benzaldehyde using heterocyclization; asym. dihydroxylation; and intramol. Suzuki-Miyaura reaction as key steps); Heterocyclization; Macrocyclization; Stereoselective synthesis (stereoselective prepn. of fragments of complestatin and chloropeptin I starting from nitroaniline and dihydroxy(iodo)benzaldehyde using heterocyclization; asym. dihydroxylation; and intramol. Suzuki-Miyaura reaction as key steps); Cyclic peptides Role: SPN (Synthetic preparation); PREP (Preparation) (stereoselective prepn. of fragments of complestatin and chloropeptin I starting from nitroaniline and dihydroxy(iodo)benzaldehyde using heterocyclization; asym. dihydroxylation; and intramol. Suzuki-Miyaura reaction as key steps); Dihydroxylation (stereoselective; stereoselective prepn. of fragments of complestatin and chloropeptin I starting from nitroaniline and dihydroxy(iodo)benzaldehyde using heterocyclization; asym. dihydroxylation; and intramol. Suzuki-Miyaura reaction as key steps); complestatin chloropeptin I cyclotripeptide fragment asym prepn
Note
CAN 147:166593
34-3
Amino Acids, Peptides, and Proteins
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
99-09-2 (3-Nitroaniline); 4248-19-5 (tert-Butyl carbamate); 26973-43-3; 54246-05-8 (3,4-Dihydroxy-5-iodobenzaldehyde); 73183-34-3; 400778-04-3 Role: RCT (Reactant), RACT (Reactant or reagent) (stereoselective prepn. of fragments of complestatin and chloropeptin I starting from nitroaniline and dihydroxy(iodo)benzaldehyde using heterocyclization, asym. dihydroxylation, and intramol. Suzuki-Miyaura reaction as key steps); 5459-50-7P (2-Iodo-5-nitroaniline); 854443-88-2P; 854443-93-9P; 943975-78-8P; 943975-79-9P; 943975-80-2P; 943975-81-3P; 943975-82-4P; 943975-83-5P; 943975-84-6P; 943975-86-8P; 943975-87-9P; 943975-88-0P; 943975-89-1P; 943975-90-4P; 943975-91-5P; 943975-92-6P; 943975-93-7P; 943975-95-9P; 943975-96-0P; 943975-97-1P; 943975-98-2P; 944060-67-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (stereoselective prepn. of fragments of complestatin and chloropeptin I starting from nitroaniline and dihydroxy(iodo)benzaldehyde using heterocyclization, asym. dihydroxylation, and intramol. Suzuki-Miyaura reaction as key steps); 943975-85-7P; 943975-94-8P; 944060-68-8P Role: SPN (Synthetic preparation), PREP (Preparation) (stereoselective prepn. of fragments of complestatin and chloropeptin I starting from nitroaniline and dihydroxy(iodo)benzaldehyde using heterocyclization, asym. dihydroxylation, and intramol. Suzuki-Miyaura reaction as key steps)
34-3
Amino Acids, Peptides, and Proteins
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
99-09-2 (3-Nitroaniline); 4248-19-5 (tert-Butyl carbamate); 26973-43-3; 54246-05-8 (3,4-Dihydroxy-5-iodobenzaldehyde); 73183-34-3; 400778-04-3 Role: RCT (Reactant), RACT (Reactant or reagent) (stereoselective prepn. of fragments of complestatin and chloropeptin I starting from nitroaniline and dihydroxy(iodo)benzaldehyde using heterocyclization, asym. dihydroxylation, and intramol. Suzuki-Miyaura reaction as key steps); 5459-50-7P (2-Iodo-5-nitroaniline); 854443-88-2P; 854443-93-9P; 943975-78-8P; 943975-79-9P; 943975-80-2P; 943975-81-3P; 943975-82-4P; 943975-83-5P; 943975-84-6P; 943975-86-8P; 943975-87-9P; 943975-88-0P; 943975-89-1P; 943975-90-4P; 943975-91-5P; 943975-92-6P; 943975-93-7P; 943975-95-9P; 943975-96-0P; 943975-97-1P; 943975-98-2P; 944060-67-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (stereoselective prepn. of fragments of complestatin and chloropeptin I starting from nitroaniline and dihydroxy(iodo)benzaldehyde using heterocyclization, asym. dihydroxylation, and intramol. Suzuki-Miyaura reaction as key steps); 943975-85-7P; 943975-94-8P; 944060-68-8P Role: SPN (Synthetic preparation), PREP (Preparation) (stereoselective prepn. of fragments of complestatin and chloropeptin I starting from nitroaniline and dihydroxy(iodo)benzaldehyde using heterocyclization, asym. dihydroxylation, and intramol. Suzuki-Miyaura reaction as key steps)
Laboratories
LSPN
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Scientific production and competences > SB - School of Basic Sciences > ISIC - Institute of Chemical Sciences and Engineering > LSPN - Laboratory of synthesis and natural products
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Published
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Record creation date
2010-11-25