A synthesis of the diazonamide heteroaromatic biaryl macrocycle/hemiaminal core.
[reaction: see text] Stille coupling of an arylstannane aminal 19 with the palladium complex 23 leads to atropisomeric esters 28 and 29. Conversion to macrocycle 30 is demonstrated, a potential precursor of natural and unnatural diazonamides.
Zajac
Matthew A
MA
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.
Vedejs
Edwin
E
D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis*; D010165:Palladium / Q000737:chemistry
D006576:Heterocyclic Compounds, 4 or More Rings; D010080:Oxazoles; C408862:diazonamide A; D010165:Palladium