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- W2010046098 abstract "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 cyclization. However, this work spawned a second-generation strategy in which the spirocycle was fashioned via a radical-polar crossover reaction. This process merged an intramolecular radical conjugate addition with an enolate hydroxylation and created two stereocenters with excellent diastereoselectivity. The reaction was promoted by irradiation with a sunlamp, and a ditin reagent was required for aryl radical formation. These facts suggest that the substrate may function as a sensitizer, thereby facilitating homolytic cleavage of the ditin reagent. The propellane motif of the target was then installed via annulation of a pyrrolidine ring onto the spirocycle. The sequence of reactions used included a phenolic oxidation, an asymmetric ketone allylation mediated by Nakamura's chiral allylzinc reagent, an anionic oxy-Cope rearrangement, a one-pot ozonolysis-reductive amination, and a Lewis acid promoted cyclization of an amine onto an alpha,beta-unsaturated dimethyl ketal. Further studies of the asymmetric ketone allylation demonstrated the ability of the Nakamura reagent to function well in a mismatched situation. A TiCl(4)-catalyzed regioselective methyl enol etherification of a 1,3-diketone completed the synthesis." @default.
- W2010046098 created "2016-06-24" @default.
- W2010046098 creator A5043698481 @default.
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- W2010046098 date "2009-11-11" @default.
- W2010046098 modified "2023-10-18" @default.
- W2010046098 title "Enantioselective Total Synthesis of (−)-Acutumine" @default.
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- W2010046098 doi "https://doi.org/10.1021/jo902006q" @default.
- W2010046098 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/2790369" @default.
- W2010046098 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/19904909" @default.
- W2010046098 hasPublicationYear "2009" @default.
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