122490-85-1Relevant articles and documents
New asymmetric route to bridged indole alkaloids: Formal enantiospecific syntheses of (-)-suaveoline, (-)-raumacline and (-)-Nb-methylraumacline
Bailey, Patrick D.,Collier, Ian D.,Hollinshead, Sean P.,Moore, Madeleine H.,Morgan, Keith M.,Smith, David I.,Vernon, John M.
, p. 1209 - 1214 (2007/10/03)
The homologous nitrile 13 derived from L-tryptophan undergoes a modified Pictet-Spengler reaction with methyl propynoate, under conditions of kinetic control, to afford the cis-tetrahydro-β-carboline 15a (cis:trans = 77:23). After protection, Dieckmann-Thorpe cyclisation to the bridged keto nitrile 20 proceeds in 90% yield. Simple functional group modifications via the alcohol 21a and nitrile 22 (structures confirmed by X-ray crystallography) allow convergence with the tetracyclic α,β-unsaturated aldehyde 10, which is an advanced intermediate for the synthesis of a range of bridged indole alkaloids.
Pictet-Spengler reactions in aprotic media. The total synthesis of (±) suaveoline
Trudell,Soerens,Weber,Hutchins,Grubisha,Bennett,Cook
, p. 1805 - 1822 (2007/10/02)
The first total synthesis of the indole alkaloid (±)-suaveoline 1 (a macroline-related base and a member of the sarpagine/ajmaline class of alkaloids) was completed in a stereocontrolled fashion. The serial synthesis employed three intramolecular reaction
