A formal synthesis of porantheridine and an epimer.
A formal synthesis of porantheridine and a synthesis of its C6-epimer have been completed, employing silver-catalyzed allene cyclization to form a common cis-isoxazolidine intermediate and related N-acyl iminium ion intermediates for side-chain introduction. The stereochemistry of this step can be controlled by choice of the N-protection method.
Bates
Roderick W
RW
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, 21 Nanyang Link, Nanyang Technological University, Singapore 637371. roderick@ntu.edu.sg
Lu
Yongna
Y
D000215:Acylation; D000466:Alkadienes / Q000737:chemistry; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006046:Gold / Q000737:chemistry*; D007097:Imines / Q000737:chemistry; D008956:Models, Chemical; D010080:Oxazoles / Q000737:chemistry; D012834:Silver / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism
D000466:Alkadienes; D000470:Alkaloids; D007097:Imines; D010080:Oxazoles; D012997:Solvents; C450779:porantheridine; C064210:oxazolidine; D012834:Silver; C025947:propadiene; D006046:Gold