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

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.

Synthesis of arieianal, a prenylated benzoic acid from Piper arieianum.

Arieianal (1) is a complex prenylated benzoic acid that was isolated from Piper arieianum. It has been synthesized through a convergent sequence that joins a functionalized diterpenoid chain to a protected aromatic core. Key steps include use of a copper enolate for selective displacement of an allylic bromide in the presence of an allylic acetate and a stereoselective Horner-Wadsworth-Emmons condensation to afford the desired E olefin of the isoprenoid side chain.