17088-50-5Relevant academic research and scientific papers
Total syntheses of (-)-acutumine and (-)-dechloroacutumine
King, Sandra M.,Calandra, Nicholas A.,Herzon, Seth B.
, p. 3642 - 3645 (2013)
One route fits all: Syntheses of the title complex tetracyclic alkaloids are described. The routes feature the strategic application of 5-trimethylsilylcyclopentadiene, a selective hydrostannylation of a complex enyne, a Hosomi-Sakurai cyclization to form the skeleton of the targets, an allylic formate rearrangement to construct the spirocyclopentenone rings, and a selective hydrogenation to establish the alkyl chloride functional group of (-)-acutumine. Copyright
Total synthesis of (-)-acutumine
Li, Fang,Tartakoff, Samuel S.,Castle, Steven L.
supporting information; experimental part, p. 6674 - 6675 (2009/10/30)
(Chemical Equation Presented) The first total synthesis of the tetracyclic alkaloid (-)-acutumine is described. Key reactions include an asymmetric ketone allylation mediated by Nakamura's chiral allylzinc reagent, an anionic oxy-Cope rearrangement, and t
Enantioselective total synthesis of (-)-acutumine
Li, Fang,Tartakoff, Samuel S.,Castle, Steven L.
experimental part, p. 9082 - 9093 (2010/03/04)
(Chemical Equation Presented) An account of the total synthesis of the tetracyclic alkaloid (-)-acutumine is presented. A first-generation approach to the spirocyclic subunit was unsuccessful as a result of incorrect regioselectivity in a radical cyclizat
