An N-acyliminium cyclization approach to a total synthesis of (+)-cylindricine C.
[reaction: see text] Details of problems and solutions encountered during the development of an enantioselective total synthesis of (+)-cylindricine C are described here. The total synthesis itself was accomplished in 8 steps, featuring an N-acyliminium cyclization strategy, the seldom-used Wharton rearrangement, and a key epimerization at C5.
Liu
Jia
J
Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.
Swidorski
Jacob J
JJ
Peters
Scott D
SD
Hsung
Richard P
RP
D000215:Acylation; D003500:Cyclization; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D015363:Quinolones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D006575:Heterocyclic Compounds, 3-Ring; D007097:Imines; D015363:Quinolones; C485391:cylindricine C