2-Cyano Δ3 piperideines VIII : Biomimetic approach to the synthesis of the decahydroquinoline ring system of poison-dart frog toxins

✍ Scribed by M. Bonin; R. Besselièvre; D.S. Grierson; H.-P. Husson

• Publisher: Elsevier Science
• Year: 1983
• Tongue: French
• Weight: 270 KB
• Volume: 24
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)81690-1

✦ Synopsis

A biomimetic approach towards the synthesis of pumiliotoxin C has been developed.The key transformation of enamine equivalent 8 to 2 was catalyzed by contact with alumina. Cyclized intermediate 2 was then reduced stereospecifically to the trans ----decahydroquinoline 11 or stereoselectively to the cis compound 12.-_---Recent and intense interest has been directed towards the total synthesis of the poison-dart frog toxin; pumiliotoxin-C2 1 and gephyrotoxin 23 due to their interesting pharmacological activities . Both compounds T and 2 possess a c%-decahydroquinoline ring system with side chain substituents at the C-2 and C-3 positions 5-TFhe C-2 side chain of 2 being further attached at nitrogen, forming a third ring). The relative configurations 07 these substituents are not the same, however, with the consequence that the two natural compounds adqp_topposite cis-fused conformations (conformations A and B)6. Any synthesis of these --toxins has to take into account these structural features.