93627-41-9Relevant academic research and scientific papers
Synthesis of (-)-Hobartine and Related Indole Alkaloids
Darbre, Tamis,Nussbaumer, Cornelius,Borschberg, Hans-Juerg
, p. 1040 - 1052 (1984)
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.
