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Synthesis of the Rubiyunnanin B Core Aglycon
Author(s) -
Moschitto Matthew J.,
Lewis Chad A.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600741
Subject(s) - chemistry , glycosylation , stereochemistry , amide , residue (chemistry) , suzuki reaction , combinatorial chemistry , organic chemistry , catalysis , palladium , biochemistry
Rubiyunnanin B possesses an intriguing anticancer profile whose activity is dependent on the glycosylation of a fused tyrosinyl residue. We have developed a rapid synthesis of the rubiyunnanin B dityrosine core using a Suzuki coupling. Furthermore, the atropisomeric and isomeric products obtained were identified and their distribution controlled. The two major products obtained from the dityrosine coupling were discovered to be locked cis/trans isomers of the internal amide with atropisomerization quantifiable on the NMR timescale.