Synthesis of the tetracyclic skeleton of the Lycopodium alkaloid lycopladine H via a pivotal double hydroformylation/intramolecular reductive amination sequence.

@article{Chauhan2015SynthesisOT,
  title={Synthesis of the tetracyclic skeleton of the Lycopodium alkaloid lycopladine H via a pivotal double hydroformylation/intramolecular reductive amination sequence.},
  author={Pradeep S Chauhan and Joshua R Sacher and Steven M Weinreb},
  journal={Organic letters},
  year={2015},
  volume={17 4},
  pages={
          806-8
        }
}
A synthesis of the complete tetracyclic framework of the structurally unique Lycopodium alkaloid lycopladine H has been accomplished using a strategy involving a double alkene hydroformylation/intramolecular reductive amination to form the azocane and spiro-piperidine moieties of the natural product. 
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12 Citations

12 Citations

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Citation Type

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This Dissertation is protected by copyright and/or related rights. It has been brought to you by ScholarWorks@UNO with permission from the rights-holder(s). You are free to use this Dissertation in…
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References

SHOWING 1-10 OF 20 REFERENCES
Construction of the azocane (azacyclooctane) moiety of the Lycopodium alkaloid lycopladine H via an intramolecular hydroaminomethylation strategy.
An efficient synthetic strategy has been developed for annulation of an azocane ring onto a bicyclo[2.2.2]octane scaffold via an intramolecular hydroaminomethylation protocol to generate an advanced…
Exploratory studies towards a total synthesis of the unusual bridged tetracyclic Lycopodium alkaloid lycopladine H.
Lycopladine H, a novel alkaloid with fused-tetracyclic skeleton from Lycopodium complanatum
Efficient syntheses of functionalized piperidines through extremely regioselective Rh-catalyzed cyclohydrocarbonylation of amido-ω,ω′-dienes
Lycopodium alkaloids: isolation and asymmetric synthesis.
TLDR
This review describes isolation and asymmetric syntheses of several new alkaloids such as lycoposerramines-C, -V, -W, and cernuine and shows that asymmetric total synthesis played a key role in elucidating the structures of these complex natural products.
Polycyclic molecules from linear precursors: stereoselective synthesis of clavolonine and related complex structures.
TLDR
The structure of lycopodine provides an instructive model to explore a strategy centered on a convergent synthesis of a linear precursor that contains the complete carbon backbone and the incorporation of a reaction cascade sequence to construct the remaining carbon–carbon bonds.
Short access to (+)-lupinine and (+)-epiquinamide via double hydroformylation.
Short and efficient access to (+)-lupinine and (+)-epiquinamide by means of an unprecedented double hydroformylation of a bis-homoallylic azide followed by a tandem catalytic hydrogenation/reductive…
Lycopladines F and G, new C16N2-type alkaloids with an additional C4N unit from Lycopodium complanatum
Lycopladine A, a new C16N alkaloid from Lycopodium complanatum
Lycopladine E, a new C16N1-type alkaloid from Lycopodium complanatum
A new C 16 N 1 -type alkaloid, lycopladine E (1), has been isolated from the club moss Lycopodium complanatum, and the structure and absolute stereochemistry were elucidated on the basis of…
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