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Connecting Tyrosine and Tryptophan Units of Diazonamide A and Azonazine by a Diastereodivergent Arylative Dearomatization
Author(s) -
Denizot Natacha,
Guillot Régis,
Kouklovsky Cyrille,
Vincent Guillaume
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201503612
Subject(s) - stereocenter , tryptophan , tyrosine , stereoselectivity , stereochemistry , chemistry , organic chemistry , amino acid , biochemistry , catalysis , enantioselective synthesis
We report the Friedel–Crafts coupling of a tyrosine unit with tryptophan‐derived pyrrolindolenium ions which are configurationally stable. The reaction allowed the stereoselective and divergent access to the required quaternary stereocenters found in diazonamide A and azonazine at the junction of the tyrosine and tryptophan units.