research article

Studies toward the total synthesis of RP-66453

Boisnard, Sabine
•
Zhu, Jieping  
2002
Tetrahedron Letters

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)]

Cite this item

Boisnard, S., & Zhu, J. (2002). Studies toward the total synthesis of RP-66453. Tetrahedron Letters, 43(14), 2577–2580. https://doi.org/10.1016/S0040-4039(02)00307-6

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Type
research article
DOI
10.1016/S0040-4039(02)00307-6
Author(s)
Boisnard, Sabine
Zhu, Jieping  
Date Issued

2002

Publisher

Elsevier

Published in
Tetrahedron Letters
Volume

43

Issue

14

Start page

2577

End page

2580

Subjects

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)

Editorial or Peer reviewed

REVIEWED

Written at

OTHER

EPFL units
LSPN  
Available on Infoscience
November 25, 2010
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/58506