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Please use this identifier to cite or link to this item: http://dspace.utalca.cl/handle/1950/9142

Title: Short Total Synthesis of (-)-Lupinine and (-)-Epiquinamide by Double Mitsunobu Reaction
Authors: Santos, L.S.
Mirabal-Gallardo, Y.
Shankaraiah, N.
Simirgiotis, M.J.
Keywords: quinolizidine alkaloids
azido reduction
nickel boride
microwave irradiation
Mitsunobu reaction
Issue Date: 2011
Citation: SYNTHESIS-STUTTGART Issue: 1 Pages: 51-56 DOI: 10.1055/s-0030-1258356
Abstract: Alternative total syntheses of (-)-lupinine (1) and (-)-epiquinamide (2) have been described via the key intermediate 3 obtained from the addition of 2-trialkylsilyloxyfuran 5 to N-acyliminium intermediate derived from 4. The major R, R-isomer 8 obtained from the Mannich reaction was converted into its R, S-isomer through Mitsunobu reaction. Then, a second Mitsunobu reaction of 3 led to cyano 9 and azido 11 derivatives, which were converted into 1 and 2 in 33 and 36% overall yield from 4, respectively. The synthetic route is amenable for the generation of several quinolizidine alkaloids.
Description: Santos, LS (Silva Santos, Leonardo. Univ Talca, Chem Inst Nat Resources, Lab Asymmetr Synth, Talca, Chile
URI: http://dspace.utalca.cl/handle/1950/9142
ISSN: 0039-7881
Appears in Collections:Artículos en publicaciones ISI - Universidad de Talca

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