Beilstein J. Org. Chem.2008,4, No. 5, doi:10.1186/1860-5397-4-5
was then effected by first treating the thiolactam with ethyl bromoacetate, after which reaction of the resulting S-alkylated intermediate with triethylphosphite and triethylamine in acetonitrile gave the vinylogous urethane (+)-28 in 75% yield.
At this stage, however, our fears of the discrepant
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Graphical Abstract
Figure 1:
Representative quinolizidine alkaloids from amphibians.
Beilstein J. Org. Chem.2005,1, No. 17, doi:10.1186/1860-5397-1-17
72 Zlín, Czech Republic Zentiva, U Kabelovny 130, 10237 Prague 10, Czech Republic 10.1186/1860-5397-1-17 Abstract Substituted 3-(fluoroacyloxy)quinoline-2,4(1H,3H)-diones including 3-(fluoroiodoacetoxy) derivatives react with triethylphosphite to afford either the product of the Perkow reaction or
the sugar skeleton and its multiple acetoxy groups.
In this communication we would like to report on the ability of halocarboxylate anions to act as leaving groups in the reactions of 3-(haloacyloxy)-quinoline-2,4(1H,3H)-diones with triethylphosphite to afford 8 and 9, the products of the Perkow
-3-(fluoroiodoacetoxy)quinoline-2,4(1H,3H)-dione (4) was reacted with triethylphosphite an unexpected product 9 (Scheme 3) was obtained instead of the desired Horner-Wadsworth-Emmons intermediate 1-benzyl-3-butyl-3-(diethoxyphosphoryl)fluoroacetyloxy-quinoline-2,4(1H,3H)-dione. We assume the newly