1662688-34-7

Usage

Uses

Used in Medicinal Chemistry:
(2S,5S,12bS,13R,E)-3-ethylidene-5-methyl-1,2,3,4,5,6,7,12b-octahydro-2,12-methanoindolo[2,3-a]quinolizin-5-ium-13-carboxylate is used as a compound in medicinal chemistry for its potential role in drug development and biological research. Its specific molecular structure and functional groups may offer unique properties that could be harnessed for therapeutic applications, pending further investigation and analysis.

Upstream product

• 32789-73-4 20E-[3S^*-(3α,15α)]-3,4,5,6,14,15,21-heptahydro-15-(methyl acetate)-20-ethylidene-indolo[2,3-a]quinolizine 
• 1309597-54-3 (Z,2R,12bS)-tert-butyl 2-[di(methoxycarbonyl)methyl]-3-ethylidene-1,2,3,4,6,7-hexahydroindolo[2,3-a]quinolizine-12(12bH)-carboxylate 
• 153-94-6 D-tryptophan 
• 295788-92-0 (2R,6R,12bS,E)-benzyl 3-ethylidene-2-(2-methoxy-2-oxoethyl)-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine-6-carboxylate 
• 236750-92-8 20E-[3S^*-(3α,5β,15α)]-3,4,5,6,14,15,21-heptahydro-15-(methyl acetate)-20-ethylidene-indolo[2,3-a]quinolizine-5-carboxylic acid 
• 74-88-4 methyl iodide 
• 6393-66-4 (+/-)-epi-pleiocarpamine 

Relevant academic research and scientific papers

Total Syntheses of Pleiocarpamine, Normavacurine, and C-Mavacurine

The total syntheses of C-mavacurine-type indole alkaloids, (±)-pleiocarpamine, (±)-normavacurine, and (±)-C-mavacurine, were accomplished. The key step in the syntheses was the cyclization between the metal carbenoid at C16 and the N1 position in a Corynanthe-type compound that was equipped with a diazo function. For this cyclization, the N4 modification of the substrate using an amine-borane complex was indispensable to fix the molecular conformation.

Bioinspired Oxidative Cyclization of the Geissoschizine Skeleton for Enantioselective Total Synthesis of Mavacuran Alkaloids

Reported is the enantioselective total syntheses of mavacuran alkaloids, (+)-taberdivarine H, (+)-16-hydroxymethyl-pleiocarpamine, and (+)-16-epi-pleiocarpamine, and their postulated biosynthetic precursor 16-formyl-pleiocarpamine. This family of monoterp

Bioinspired Divergent Oxidative Cyclizations of Geissoschizine: Total Synthesis of (–)-17-nor-Excelsinidine, (+)-16-epi-Pleiocarpamine, (+)-16-Hydroxymethyl-Pleiocarpamine and (+)-Taberdivarine H

We report a full account of our efforts towards bioinspired oxidative cyclizations of geissochizine and analogs to mimic the biosynthesis of the mavacuran, akuammilan, and excelsinidine groups of monoterpene indole alkaloids. The construction of the A,B,C,D ring system of geissoschizine was first achieved by merging two known syntheses of this alkaloid. Modified Ma's oxidative conditions (KHMDS/I2) applied directly to geissoschizine induced formation of the N4–C16 bond encountered in the excelsinidines core. Identical conditions applied to C16-dimethylmalonate-containing N4-quaternized substrates ended in the formation of the mavacurans core (N1–C16 bond). With this unified oxidative cyclization strategy: (–)-17-nor-excelsinidine, (+)-16-epi-pleiocarpamine, (+)-16-hydroxymethyl-pleiocarpamine, 16-formyl-pleiocarpamine and (+)-taberdivarine H were synthetized. We also report a shortened total synthesis of 16-epi-pleiocarpamine compared to our preliminary communication from a C16-monoester analog. Alternatively, 17-nor-excelsinidine was synthesized via an intramolecular nucleophilic substitution of a 7-membered ring α-chlorolactam prepared from 16-desformyl-geissoschizine.