Studies on the Total Synthesis of RP 66453: Synthesis of Fully Functionalized 15-Membered Biaryl-Containing Macrocycle
2001
Abstract
Palladium-catalyzed Suzuki cross-coupling, Corey's enantioselective alkylation of glycine template, and macrolactamization are key steps in an efficient synthesis of the 15-membered macrocycle I, the A-B biaryl macrocyclic component of RP-66453 (II). Unfortunately, the cyclization of I by various methods (varying the base, the solvent and the temp.) did not provide the desired macrocycle II. [on SciFinder (R)]
Details
Title
Studies on the Total Synthesis of RP 66453: Synthesis of Fully Functionalized 15-Membered Biaryl-Containing Macrocycle
Author(s)
Boisnard, Sabine ; Carbonnelle, Anny-Claude ; Zhu, Jieping
Published in
Organic Letters
Volume
3
Issue
13
Pages
2061-2064
Date
2001
ISSN
1523-7060
Keywords
Macrocyclic compounds Role: SPN (Synthetic preparation); PREP (Preparation) (biaryl; total synthesis of the fully functionalized biaryl; macrocyclic component of RP-66453); Cyclization (lactamization; total synthesis of the fully functionalized biaryl; macrocyclic component of RP-66453); Alkylation (stereoselective; Corey; total synthesis of the fully functionalized biaryl; macrocyclic component of RP-66453); Suzuki coupling reaction (total synthesis of the fully functionalized biaryl; macrocyclic component of RP-66453); RP66453 biaryl macrocycle component total synthesis
Note
CAN 135:137701
34-3
Amino Acids, Peptides, and Proteins
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
219601-70-4 Role: CAT (Catalyst use), USES (Uses) (total synthesis of the fully functionalized biaryl, macrocyclic component of RP-66453); 174698-43-2P Role: PNU (Preparation, unclassified), PREP (Preparation) (total synthesis of the fully functionalized biaryl, macrocyclic component of RP-66453); 75-26-3 (Isopropyl bromide); 121-33-5 (Vanillin); 3160-59-6; 81477-94-3; 113850-71-8; 178744-39-3 Role: RCT (Reactant), RACT (Reactant or reagent) (total synthesis of the fully functionalized biaryl, macrocyclic component of RP-66453); 2973-76-4P; 16414-34-9P; 351442-23-4P; 351442-24-5P; 351442-25-6P; 351442-26-7P; 351442-28-9P; 351442-30-3P; 351442-31-4P; 351442-33-6P; 351442-34-7P; 351442-36-9P; 351442-38-1P; 351442-40-5P; 351442-43-8P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (total synthesis of the fully functionalized biaryl, macrocyclic component of RP-66453); 351442-21-2P Role: SPN (Synthetic preparation), PREP (Preparation) (total synthesis of the fully functionalized biaryl, macrocyclic component of RP-66453)
34-3
Amino Acids, Peptides, and Proteins
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
219601-70-4 Role: CAT (Catalyst use), USES (Uses) (total synthesis of the fully functionalized biaryl, macrocyclic component of RP-66453); 174698-43-2P Role: PNU (Preparation, unclassified), PREP (Preparation) (total synthesis of the fully functionalized biaryl, macrocyclic component of RP-66453); 75-26-3 (Isopropyl bromide); 121-33-5 (Vanillin); 3160-59-6; 81477-94-3; 113850-71-8; 178744-39-3 Role: RCT (Reactant), RACT (Reactant or reagent) (total synthesis of the fully functionalized biaryl, macrocyclic component of RP-66453); 2973-76-4P; 16414-34-9P; 351442-23-4P; 351442-24-5P; 351442-25-6P; 351442-26-7P; 351442-28-9P; 351442-30-3P; 351442-31-4P; 351442-33-6P; 351442-34-7P; 351442-36-9P; 351442-38-1P; 351442-40-5P; 351442-43-8P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (total synthesis of the fully functionalized biaryl, macrocyclic component of RP-66453); 351442-21-2P Role: SPN (Synthetic preparation), PREP (Preparation) (total synthesis of the fully functionalized biaryl, macrocyclic component of RP-66453)
Laboratories
LSPN
Record Appears in
Scientific production and competences > SB - School of Basic Sciences > ISIC - Institute of Chemical Sciences and Engineering > LSPN - Laboratory of synthesis and natural products
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Record creation date
2010-11-25