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. 2011 Jun 17;13(12):3222-5.
doi: 10.1021/ol2011242. Epub 2011 May 26.

Acetoxy Meldrum's acid: a versatile acyl anion equivalent in the Pd-catalyzed asymmetric allylic alkylation

Barry M Trost  1 , Maksim Osipov, Philip S J Kaib, Mark T Sorum
Affiliations

Acetoxy Meldrum's acid: a versatile acyl anion equivalent in the Pd-catalyzed asymmetric allylic alkylation

Barry M Trost et al. Org Lett. .

Abstract

Acetoxy Meldrum's acid can serve as a versatile acyl anion equivalent in the Pd-catalyzed asymmetric allylic alkylation. The reaction of this nucleophile with various meso and racemic electrophiles afforded alkylated products in high yields and enantiopurities. These enantioenriched products are versatile intermediates that can be further functionalized using nitrogen- and oxygen-centered nucleophiles, affording versatile scaffolds for the synthesis of nucleoside analogues. These scaffolds were used to complete formal syntheses of the anti-HIV drugs carbovir, abacavir, and the antibiotic aristeromycin.

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Figures

Figure 1
Figure 1
Strategies to access nucleoside analogues
Scheme 1
Scheme 1
Formal Syntheses of Carbovir, Abacavir, and Aristeromycin
See this image and copyright information in PMC

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