Total syntheses and their biological evaluation of poison-frog al | 58066
Journal of Clinical Trials

Journal of Clinical Trials
Open Access

ISSN: 2167-0870

+44 7868 792050

Total syntheses and their biological evaluation of poison-frog alkaloids ent-cis-195A and cis-211A

Joint Event on 7th International Conference on Clinical Trials & 12th World CADD & Drug Delivery Summit

September 24-26, 2018 | Chicago, USA

Naoki Toyooka

University of Toyama, Japan

Scientific Tracks Abstracts: J Clin Trials

Abstract :

To date, over 800 lipophilic alkaloids representing more than 20 structural classes have been detected from the skin extracts of neotropical poison frogs. The 2,5-disubstituted decahydroquinolines are represented one of the major classes, and the structural diversity and pharmacological activity associated with this class of alkaloids have stimulated synthetic activity in numerous groups. We report here the first total synthesis of the decahydroquinoline type poison-frog alkaloid cis-211A along with ent-cis-195A. The synthesis began with known piperidine 16, which was converted to aminoester 2 in 3 steps. Michaeltype conjugate addition reaction of 2 provided the adduct 3 in high yield as a single stereoisomer. The ester 3 was transformed into the keto-aldehyde 4, which was subjected to an intermolecular aldol-type cyclization to afford the cis-fused enone 5 as a single isomer. The conjugate addition reaction of 5 followed by treatment of the resulting enolate with Cominsā?? reagent gave rise to the common and key intermediate of enol triflates 6. Synthesis of ent-cis-195A was achieved from 6 in 2 steps, and the first total synthesis of cis-211A was also completed from 6 in 5 steps as shown in Scheme1. Details of the synthetic process synthesis and their evaluation of the nicotinic acetylcholine receptors and inhibitory effect on [3H] nicotine uptake by TRBBB13 cells of both synthetic alkaloids will be reported.

Biography :