Extending Pummerer reaction chemistry. Synthesis studies in the phakellin alkaloid area.
The syntheses of (+/-)-dibromophakellstatin and, from this species, (+/-)-dibromophakellin are described. Oxidative cyclization of a phenylthiolated dihydrooroidin derivative triggered by a Pummerer reaction constitutes the key step in this biomimetic approach to this family of marine alkaloids.
Feldman
Ken S
KS
Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA. ksf@chem.psu.edu
Skoumbourdis
Amanda P
AP
Fodor
Matthew D
MD
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods*; D003500:Cyclization; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D007093:Imidazoles; D010879:Piperazines; C104805:dibromophakellstatin; C465248:phakellin