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. 2012 Oct 28;68(43):8937-8941.
doi: 10.1016/j.tet.2012.08.020.

Formal Synthesis of 4-diphosphocytidyl-2-C-methyl D-erythritol From D-(+)-Arabitol

Sina I Odejinmi  1 , Rafael G Rascon, Wyman Chen, Kent Lai
Affiliations

Formal Synthesis of 4-diphosphocytidyl-2-C-methyl D-erythritol From D-(+)-Arabitol

Sina I Odejinmi et al. Tetrahedron. .

Abstract

2-C-methyl-D-erythritol-4-phosphate (MEP) is a key chemical intermediate of the non-mevalonate pathway for isoprenoid biosynthesis employed by many pathogenic microbes. MEP is also the precursor for the synthesis of 4-diphosphocytidyl-2-C-methyl D-erythritol (CDP-ME), another key intermediate of the non-mevalonate pathway. As this pathway is non-existent in higher animals, including humans, it represents great opportunities for novel antimicrobial development. To facilitate the in-depth studies of this pathway, we reported here a formal synthesis of CDP-ME through a new synthesis of 2-C-Methyl-D-erythritol-4-phosphoric acid from D-(+)-arabitol.

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Figures

Scheme 1
Scheme 1
Benzylidene formation by catalytic HCl.
Scheme 2
Scheme 2
Preparation of dioxanone through a selective monophosphorylation and Dess-Martin periodinane oxidation.
Scheme 3
Scheme 3
Selective alkylation and global deprotection.a a 1H and 31P NMR spectra of CDP-ME are given in the Supplementary Data.
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