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|Title: ||Short Total Synthesis of (-)-Lupinine and (-)-Epiquinamide by Double Mitsunobu Reaction|
|Authors: ||Santos, L.S.|
|Keywords: ||quinolizidine alkaloids|
|Issue Date: ||2011 |
|Publisher: ||GEORG THIEME VERLAG KG|
|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|
|Appears in Collections:||Artículos en publicaciones ISI - Universidad de Talca|
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