Synthesis of the 4-azatricyclo[5.2.2.0(4,8)]undecan-10-one core of daphniphyllum alkaloid calyciphylline A using a Pd-catalyzed enolate alkenylation.
[reaction: see text] The ABC ring system of the natural product calyciphylline A has been synthesized. The key steps were a palladium-catalyzed intramolecular coupling of an amino-tethered vinyl bromide with a ketone using potassium phenoxide as the base to generate the C-ring and a hydroxyl-directed hydrogenation of an exocyclic double bond to give the azatricyclic ketone 1.
Solé
Daniel
D
Laboratori de Química Orgànica, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII s/n, 08028-Barcelona, Spain.
Urbaneja
Xavier
X
Bonjoch
Josep
J
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006572:Heterocyclic Compounds, Bridged-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D031995:Saxifragaceae / Q000737:chemistry
D000470:Alkaloids; D006572:Heterocyclic Compounds, Bridged-Ring; D011083:Polycyclic Compounds; C479143:calyciphylline A; D010165:Palladium