research article

A formal total synthesis of deoxybouvardin

Bigot, Antony
•
Beugelmans, Rene
•
Zhu, Jieping  
1997
Tetrahedron

A synthesis of L,L-N,N-dimethylcycloisodityrosine (I) based on an intramol. SNAr reaction is reported. A possible explanation was proposed to account for the facile epimerization encountered in the cycloetherification of dipeptide L,L-II and a soln. to this problem led to a formal total synthesis of deoxybouvardin. [on SciFinder (R)]

Cite this item

Bigot, A., Beugelmans, R., & Zhu, J. (1997). A formal total synthesis of deoxybouvardin. Tetrahedron, 53(31), 10753–10764. https://doi.org/10.1016/S0040-4020(97)00706-0

Click Copy to copy the citation, or select the text manually.

Type
research article
DOI
10.1016/S0040-4020(97)00706-0
Author(s)
Bigot, Antony
Beugelmans, Rene
Zhu, Jieping  
Date Issued

1997

Published in
Tetrahedron
Volume

53

Issue

31

Start page

10753

End page

10764

Subjects

deoxybouvardin formal total synthesis; intramol nucleophilic arom substitution cycloisodityrosine prepn

Note

CAN 127:205876

34-3

Amino Acids, Peptides, and Proteins

Institut de Chimie des Substances Naturelles, CNRS,Gif-Sur-Yvette,Fr.

Journal

written in English.

64725-24-2P (Deoxybouvardin) Role: PNU (Preparation, unclassified), PREP (Preparation) (formal total synthesis of deoxybouvardin via intramol. nucleophilic arom. substitution); 60-18-4 (L-Tyrosine); 160247-85-8; 178208-42-9 Role: RCT (Reactant), RACT (Reactant or reagent) (formal total synthesis of deoxybouvardin via intramol. nucleophilic arom. substitution); 82038-34-4P; 138605-22-8P; 178208-43-0P; 178208-45-2P; 178208-47-4P; 178208-49-6P; 178208-51-0P; 178208-57-6P; 178208-58-7P; 178208-59-8P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (formal total synthesis of deoxybouvardin via intramol. nucleophilic arom. substitution); 109011-08-7P; 178208-53-2P; 194655-45-3P Role: SPN (Synthetic preparation), PREP (Preparation) (formal total synthesis of deoxybouvardin via intramol. nucleophilic arom. substitution)

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/20.500.14299/58552