1897-26-3Relevant articles and documents
Enantioselective Total Syntheses of Methanoquinolizidine-Containing Akuammiline Alkaloids and Related Studies
Picazo, Elias,Morrill, Lucas A.,Susick, Robert B.,Moreno, Jesus,Smith, Joel M.,Garg, Neil K.
, p. 6483 - 6492 (2018)
The akuammiline alkaloids are a structurally diverse class of bioactive natural products isolated from plants found in various parts of the world. A particularly challenging subset of akuammiline alkaloids are those that contain a methanoquinolizidine core. We describe a synthetic approach to these compounds that has enabled the first total syntheses of (+)-strictamine, (-)-2(S)-cathafoline, (+)-akuammiline, and (-)-ψ-akuammigine. Our strategy relies on the development of the reductive interrupted Fischer indolization reaction to construct a common pentacyclic intermediate bearing five contiguous stereocenters, in addition to late-stage formation of the methanoquinolizidine framework using a deprotection-cyclization cascade. The total syntheses of (-)-ψ-akuammigine and (+)-akuammiline mark the first preparations of akuammiline alkaloids containing both a methanoquinolizidine core and vicinal quaternary centers. Lastly, we describe the bioinspired reductive rearrangements of (+)-strictamine and (+)-akuammiline to ultimately provide (-)-10-demethoxyvincorine and a new analogue thereof.
ALSTOLENINE, 19,20-DIHYDROPOLYNEURIDINE AND OTHER MINOR ALKALOIDS OF THE LEAVES OF ALSTONIA VENENATA
Majumder, Priyalal,Basu, Ashoke
, p. 2389 - 2392 (2007/10/02)
Structures of alstolenine and 19,20-dihydropolyneuridine, two new indole alkaloids of the leaves of Alstonia venenata have been established.In addition, deacetylakuammiline, polyneuridine and raucaffrinoline have been isolated for the first time from this plant.Key Word Index-Alstonia venenata; Apocynaceae; alstolenine; 19,20-dihydropolyneuridine; polyneuridine; deacetylakuammiline; raucaffrinoline; indol alkaloids.
