A formal total synthesis of deoxybouvardin

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)]


Published in:
Tetrahedron, 53, 31, 10753-10764
Year:
1997
Keywords:
Note:
CAN 127:205876
34-3
Amino Acids, Peptides, and Proteins
Institut de Chimie des Substances Naturelles, CNRS,Gif-Sur-Yvette,Fr.
Journal
0040-4020
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)
Laboratories:




 Record created 2010-11-25, last modified 2018-03-17


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