Oxazolone cycloadducts as heterocyclic scaffolds for alkaloid construction: synthesis of (+/-)-2-epi-pumiliotoxin C.
Intramolecular Diels-Alder cycloaddition of N-substituted oxazolone triene I allows direct entry to the functionalized octahydroquinoline II. Further manipulation of this framework by stereo- and regioselective introduction of the 5-methyl substituent, followed by excision of the carbamate, yields (+/-)-2-epi-pumiliotoxin C.
Fearnley
Stephen Philip
SP
Department of Chemistry, The City University of New York - The Graduate Center & York College, 94-20 Guy R. Brewer Boulevard, Jamaica, New York, 11451, USA. fearnley@york.cuny.edu
Thongsornkleeb
Charnsak
C
D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry; D003500:Cyclization; D008958:Models, Molecular; D010081:Oxazolone / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D000475:Alkenes; D011804:Quinolines; D010081:Oxazolone; C011093:pumiliotoxin C