Synthesis of 3,3',5-trihydroxybiphenyl-2-carboxylic acid, a component of the bitterest natural product amarogentin and its coenzyme A and N-acetyl cysteamine thiol esters.
3,3',5-Trihydroxybiphenyl-2-carboxylic acid (6), an ester component of the bitter-tasting natural products amarogentin and amaroswerin, was synthesized in six steps in 13.6% overall yield. Its N-acetyl cysteamine thiol ester (9) and its coenzyme A thiol ester (8), a likely biosynthetic precursor of the amarums, were also prepared.
Wang
C Z
CZ
Institut für Pharmazie, Lehrstuhl für Pharmazeutische Biologie, Universität München, Karlstrasse 29, 80333 München, Germany. wang@mail.wsu.edu
Maier
U H
UH
Zenk
M H
MH
D003065:Coenzyme A / Q000737:chemistry*; D003543:Cysteamine / Q000031:analogs & derivatives* / Q000737:chemistry; D004952:Esters; D005960:Glucosides / Q000737:chemistry*; D039823:Iridoids; D015394:Molecular Structure; D011714:Pyrans / Q000737:chemistry*; D013057:Spectrum Analysis
D004952:Esters; D005960:Glucosides; D039823:Iridoids; D011714:Pyrans; C102609:amarogentin; D003543:Cysteamine; D003065:Coenzyme A