Total synthesis of (+/-)-rhazinal using novel palladium-catalyzed cyclizations.
A concise synthesis of (+/-)-rhazinal that hinges on novel oxidative Heck cyclizations and palladium-catalyzed direct couplings is described. An X-ray structure of N-MOM-rhazinal, which provides insight into the conformation of the strained 9-membered lactam ring, is described.
Bowie
Alfred L
AL
Department of Chemistry, University of California, Berkeley, California 94720, USA.
Trauner
Dirk
D
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D000577:Amides / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D000577:Amides; D007212:Indolizines; D011758:Pyrroles; C480458:rhazinal; C035094:indolizine; D010165:Palladium