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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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Intramolecular amidofuran cycloadditions across an indole pi-bond: an efficient approach to the aspidosperma and strychnos ABCE core.

[reaction: see text] The intramolecular Diels-Alder reaction between an amidofuran moiety tethered onto an indole component was examined as a strategy for the synthesis of Aspidosperma and Strychnos alkaloids. Furanyl carbamate 13 was acylated using the mixed anhydride 16 to provide amidofuran 12 in 68% yield. Further N-acylation of this indole furnished 17 in 88% yield. Cyclization precursors were prepared by removing the carbamate moiety followed by N-alkylation with the appropriate alkyl halides. Thermolysis of 25 provided the novel tetracyclic ketone 26 in 74% yield.[1]

References

  1. Intramolecular amidofuran cycloadditions across an indole pi-bond: an efficient approach to the aspidosperma and strychnos ABCE core. Lynch, S.M., Bur, S.K., Padwa, A. Org. Lett. (2002) [Pubmed]
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