Gold-catalyzed cycloisomerization of N-Propargylindole-2-carboxamides: application toward the synthesis of lavendamycin analogues.
A series of N-propargylindole-2-carboxamides were found to undergo a AuCl 3-catalyzed cycloisomerization to give beta-carbolinones in high yield. The corresponding beta-chlorocarboline derivative was prepared and used for Pd(0)-catalyzed cross-coupling chemistry directed toward the synthesis of lavendamycin analogues.
England
Dylan B
DB
Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.
Padwa
Albert
A
D000480:Alkynes / Q000737:chemistry*; D002243:Carbolines / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D017612:Gold Compounds / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism; D013308:Streptonigrin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D000480:Alkynes; D002243:Carbolines; D017612:Gold Compounds; D007211:Indoles; D009942:Organometallic Compounds; C038016:gold chloride; D013308:Streptonigrin; D010165:Palladium; C034566:lavendamycin