Synthesis of cycloisodityrosine revisited: A selective ring forming process

An efficient synthesis of cycloisodityrosine was developed based on an intramol. nucleophilic arom. substitution reaction for the selective ring formation of a key biaryl ether intermediate. Cycloetherification of dipeptide I gave exclusively the (meta,para)-cyclophane II (R = OH, R1 = NO2, R2 = Me3CO2C, R3 = H) at the expense of the 15-membered (para,para)-cyclophane III as a result of an enthalpy controlled process. The (meta,para)-cyclophane II (R = OH, R1 = NO2, R2 = Me3CO2C, R3 = H) was easily transformed to N,N'-dimethyl cycloisodityrosine II (R = OMe, R1 = H, R2 = Me, R3 = Me), an important structural subunit of bouvardin and the RA series. [on SciFinder (R)]


Published in:
Tetrahedron Letters, 39, 7, 551-554
Year:
1998
Keywords:
Note:
CAN 128:192908
34-3
Amino Acids, Peptides, and Proteins
CNRS,Institut de Chimie des Substances Naturelles,Gif-sur-Yvette,Fr.
Journal
0040-4039
written in English.
167467-05-2P Role: PNU (Preparation, unclassified), PREP (Preparation) (synthesis of cycloisodityrosine via an efficient cycloetherification reaction); 160877-40-7; 173775-54-7; 178208-45-2; 188624-33-1; 203310-96-7 Role: RCT (Reactant), RACT (Reactant or reagent) (synthesis of cycloisodityrosine via an efficient cycloetherification reaction); 138605-22-8P; 152429-89-5P; 203310-99-0P; 203311-01-7P; 203311-03-9P; 203311-05-1P; 203311-07-3P; 203450-65-1P; 203526-43-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (synthesis of cycloisodityrosine via an efficient cycloetherification reaction); 109011-08-7P; 132539-23-2P; 178208-49-6P; 178208-51-0P; 203311-08-4P Role: SPN (Synthetic preparation), PREP (Preparation) (synthesis of cycloisodityrosine via an efficient cycloetherification reaction)
Laboratories:




 Record created 2010-11-25, last modified 2018-01-28


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