Total synthesis of dendrobate alkaloid (+)-241D, isosolenopsin and isosolenopsin A: application of a gold-catalyzed cyclization.
A new approach to total syntheses of piperidine alkaloids (+)-241D, isosolenopsin and isosolenopsin A has been developed from D-alanine. The key step to access the chiral pyridinone intermediate was achieved via a gold mediated cyclization. Finally, various reduction conditions afforded the natural products in few steps and good overall yields.
Equipe PNSCM, UMR 6226, Université de Rennes 1, 2 avenue du Pr Léon Bernard, 35043 Rennes, France. nicolas.gouault@univ-rennes1.fr
Nicolas
N
Gouault
Myriam
M
Le Roch
Gisele de Campos
Gde C
Pinto
Michèle
M
David
D000409:Alanine / Q000737:chemistry; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006046:Gold / Q000737:chemistry*; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D011728:Pyridones / Q000737:chemistry; D013237:Stereoisomerism
C413204:241D dendrobate alkaloid; D000470:Alkaloids; D010880:Piperidines; D011728:Pyridones; C002351:Solenopsin A; D006046:Gold; D000409:Alanine