Total synthesis of the bridged indole alkaloid apparicine.
An indole-templated ring-closing metathesis or a 2-indolylacyl radical cyclization constitute the central steps of two alternative approaches developed to assemble the tricyclic ABC substructure of the indole alkaloid apparicine. From this key intermediate, an intramolecular vinyl halide Heck reaction accomplished the closure of the strained 1-azabicyclo[4.2.2]decane framework of the alkaloid with concomitant incorporation of the exocyclic alkylidene substituents.
Bennasar
M-Lluïsa
ML
Laboratory of Organic Chemistry, Faculty of Pharmacy, and Institut de Biomedicina, University of Barcelona, Barcelona 08028, Spain. bennasar@ub.edu
Zulaica
Ester
E
Solé
Daniel
D
Roca
Tomàs
T
García-Díaz
Davinia
D
Alonso
Sandra
S
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization
D000470:Alkaloids; C008811:pericalline