67895-57-2Relevant academic research and scientific papers
Synthesis of Aristoquinoline Enantiomers and Their Evaluation at the α3β4 Nicotinic Acetylcholine Receptor
Argade, Malaika D.,Straub, Carolyn J.,Rusali, Lisa E.,Santarsiero, Bernard D.,Riley, Andrew P.
, p. 7693 - 7697 (2021)
The first synthesis of aristoquinoline (1), a naturally occurring nicotinic acetylcholine receptor (nAChR) antagonist, was accomplished using two different approaches. Comparison of the synthetic material's spectroscopic data to that of the isolated alkaloid identified a previously misassigned stereogenic center. An evaluation of each enantiomer's activity at the α3β4 nAChR revealed that (+)-1 is significantly more potent than (-)-1. This unexpected finding suggests that naturally occurring 1 possesses the opposite absolute configuration from indole-containing Aristotelia alkaloids.
Total Synthesis of (-)-Aristoquinoline via an Intramolecular Nitrilium Ion Cyclization
Gujarati, Priyansh D.,Reber, Keith P.
, p. 1404 - 1412 (2021/12/02)
The enantioselective total synthesis of the alkaloid aristoquinoline has been achieved in seven steps and 26% overall yield. A new preparation of the useful synthetic building block (-)-α -terpinyl amine was also developed in order to avoid stoichiometric mercury reagents or azide-containing intermediates. Key steps in the optimized synthetic route include an intramolecular nitrilium ion cyclization to form the characteristic azabicyclo[3.3.1]nonane ring system and a diastereoselective reduction of the resulting imine mixture to afford the natural product. An isomer of aristoquinoline containing an exocyclic alkene was also obtained and found to exhibit unusual chromatographic and spectroscopic properties.
Synthesis of (-)-Hobartine and Related Indole Alkaloids
Darbre, Tamis,Nussbaumer, Cornelius,Borschberg, Hans-Juerg
, p. 1040 - 1052 (2007/10/02)
An improved method for obtaining optically pure (S)-(1-p-menthen-8-yl)amine (12) has led to expedient syntheses of two hypothetical biogenetic intermediates on the way (S)-N-(1-p-menthen-8-yl)-2-(3-indolyl)ethylideneamine (4).The latter has been transformed into (-)-hobartine (6) in 64percent yield via stereoselective biomimetic cyclization by treatment with HCOOH.This unambiguous synthesis establishes the hitherto unknown absolute configuration of (-)-hobartine (6).Several model cyclization reactions of N-substituted α-(terpen-8-yl)imine derivatives yielding unsaturated 3-azabicyclononane compounds are described.
