Total syntheses of (+)-cylindricines C-E and (-)-lepadiformine through a common intermediate derived from an aza-Prins cyclization and Wharton's rearrangement.
[reaction: see text] Enantioselective total syntheses of (+)-cylindricines C-E and (-)-lepadiformine through a common tricyclic intermediate are described here. These syntheses are concise and feature an aza-Prins cyclization and a seldom-used Wharton rearrangement en route to the common intermediate.
Liu
Jia
J
Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.
Hsung
Richard P
RP
Peters
Scott D
SD
D000470:Alkaloids / Q000138:chemical synthesis* / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000494:pharmacology; D001372:Aza Compounds / Q000737:chemistry*; D003500:Cyclization; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000494:pharmacology; D015363:Quinolones / Q000138:chemical synthesis* / Q000494:pharmacology; D013237:Stereoisomerism
D000470:Alkaloids; D000935:Antifungal Agents; D000970:Antineoplastic Agents; D001372:Aza Compounds; D006575:Heterocyclic Compounds, 3-Ring; D015363:Quinolones; C485393:cylindricine E; C431548:lepadiformine; C485391:cylindricine C; C485392:cylindricine D