67895-57-2Relevant articles and documents
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.
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.
