Connecting Tyrosine and Tryptophan Units of Diazonamide A and Azonazine by a Diastereodivergent Arylative Dearomatization.
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.
Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Equipe Méthodologie, Synthèse et Molécules Thérapeutiques, Univ Paris Sud, CNRS, Université Paris-Saclay, 91405, Orsay (France).
Natacha
N
Denizot
Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Equipe Méthodologie, Synthèse et Molécules Thérapeutiques, Univ Paris Sud, CNRS, Université Paris-Saclay, 91405, Orsay (France).
Régis
R
Guillot
Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Equipe Méthodologie, Synthèse et Molécules Thérapeutiques, Univ Paris Sud, CNRS, Université Paris-Saclay, 91405, Orsay (France).
Cyrille
C
Kouklovsky
Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Equipe Méthodologie, Synthèse et Molécules Thérapeutiques, Univ Paris Sud, CNRS, Université Paris-Saclay, 91405, Orsay (France). guillaume.vincent@u-psud.fr.
Guillaume
G
Vincent
D002384:Catalysis; D004151:Dipeptides / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D009861:Onium Compounds / Q000737:chemistry*; D010080:Oxazoles / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*; D013237:Stereoisomerism; D014364:Tryptophan / Q000737:chemistry*; D014443:Tyrosine / Q000737:chemistry*
D004151:Dipeptides; D006576:Heterocyclic Compounds, 4 or More Rings; D007211:Indoles; D009861:Onium Compounds; D010080:Oxazoles; D011758:Pyrroles; C555149:azonazine; C408862:diazonamide A; D014443:Tyrosine; D014364:Tryptophan
Friedel-Crafts reactions; azonazine; diazonamide A; pyrroloindoline; tyrosine