Two-step total syntheses of canthin-6-one alkaloids: new one-pot sequential Pd-catalyzed Suzuki-Miyaura coupling and Cu-catalyzed amidation reaction.
Canthin-6-one (1) and nine analogues including the naturally occurring 9-methoxycanthin-6-one (2) and amaroridine (3) are prepared rapidly and in high yields via a convergent "non-classical" strategy that focuses on construction of the central ring B. The strategy relies on concomitant Pd-catalyzed Suzuki-Miyaura C-C coupling followed by a Cu-catalyzed C-N coupling that can be achieved either stepwise or in a new one-pot protocol starting from the appropriate 8-bromo-1,5-naphthyridine.
Gollner
Andreas
A
Department of Chemistry, University of Cyprus, P.O. Box 20537, 1678 Nicosia, Cyprus.
Koutentis
Panayiotis A
PA
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D002243:Carbolines; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D026121:Indole Alkaloids; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009287:Naphthyridines / Q000138:chemical synthesis* / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D000577:Amides; D002243:Carbolines; D026121:Indole Alkaloids; D007211:Indoles; D009287:Naphthyridines; D009942:Organometallic Compounds; C453379:canthin-6-one; D010165:Palladium; D003300:Copper