A tandem Prins/Schmidt reaction approach to marine alkaloids: formal and total syntheses of lepadiformines A and C.
The tricyclic core of the cylindricine or lepadiformine families of alkaloid natural products was assembled via a Prins addition/intramolecular Schmidt rearrangement under Lewis acid conditions. Both single-pot and two-stage variations of this process were examined, with particular attention to the stereochemical outcome of the processes. This technology has been applied to a formal total synthesis of lepadiformine A and a total synthesis of lepadiformine C.
Meyer
Angelica M
AM
Department of Medicinal Chemistry, University of Kansas, Structural Biology Center, 2121 Simons Drive, West Campus, Lawrence, Kansas 66047, USA.
Katz
Christopher E
CE
Li
Sze-Wan
SW
Vander Velde
David
D
Aubé
Jeffrey
J
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D026902:Potassium Channel Blockers / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D026902:Potassium Channel Blockers; C431548:lepadiformine