Abstract
Synthesis of a bicyclic A-B-O-C ring system of RP-66453 (I), a neurotensine receptor antagonist, with an endo aryl-aryl and an endo aryl-aryl ether bond is described. An alternative synthetic strategy starting from the construction of functionalized B-O-C cycloisodityrosine unit is also detailed. [on SciFinder (R)]
Details
Title
Studies toward the total synthesis of RP-66453
Author(s)
Boisnard, Sabine ; Zhu, Jieping
Published in
Tetrahedron Letters
Volume
43
Issue
14
Pages
2577-2580
Date
2002
ISSN
0040-4039
Keywords
Substitution reaction (arom.; prepn. of bicyclic A-B-O-C ring system of RP-66453 using intramol. SNAr reaction); Peptides Role: SPN (Synthetic preparation); PREP (Preparation) (cyclic; prepn. of bicyclic A-B-O-C ring system of RP-66453); Methylation; Suzuki coupling reaction (prepn. of bicyclic A-B-O-C ring system of RP-66453 using); Etherification (prepn. of bicyclic A-B-O-C ring system of RP-66453 using cycloetherification); Macrocyclic compounds Role: RCT (Reactant); SPN (Synthetic preparation); PREP (Preparation); RACT (Reactant or reagent) (prepn. of bicyclic A-B-O-C ring system of RP-66453 using cycloetherification); Alkylation (stereoselective; prepn. of bicyclic A-B-O-C ring system of RP-66453 using); Suzuki coupling enantioselective alkylation etherification methylation prepn cyclic peptide; nucleophilic substitution reaction prepn macrocyclic RP66453 ring system
Note
CAN 137:93981
34-3
Amino Acids, Peptides, and Proteins
CNRS, Institut de Chimie des Substances Naturelles,Gif-sur-Yvette,Fr.
Journal
written in English.
442528-03-2P; 442528-04-3P; 442528-05-4P; 442528-06-5P; 442648-41-1P; 442648-44-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and reaction of in the prepn. of bicyclic A-B-O-C ring system of RP-66453); 174698-43-2 Role: MSC (Miscellaneous) (prepn. of bicyclic A-B-O-C ring system of); 442528-07-6P; 442648-47-7P; 442648-50-2P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of bicyclic A-B-O-C ring system of RP-66453); 44605-74-5; 351442-21-2; 351442-24-5; 442528-02-1 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of in the prepn. of bicyclic A-B-O-C ring system of RP-66453)
34-3
Amino Acids, Peptides, and Proteins
CNRS, Institut de Chimie des Substances Naturelles,Gif-sur-Yvette,Fr.
Journal
written in English.
442528-03-2P; 442528-04-3P; 442528-05-4P; 442528-06-5P; 442648-41-1P; 442648-44-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and reaction of in the prepn. of bicyclic A-B-O-C ring system of RP-66453); 174698-43-2 Role: MSC (Miscellaneous) (prepn. of bicyclic A-B-O-C ring system of); 442528-07-6P; 442648-47-7P; 442648-50-2P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of bicyclic A-B-O-C ring system of RP-66453); 44605-74-5; 351442-21-2; 351442-24-5; 442528-02-1 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of in the prepn. of bicyclic A-B-O-C ring system 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