Synthesis of Enantiopure 2-C-Methyl-d-erythritol 4-Phosphate and 2,4-Cyclodiphosphate from d-Arabitol

Synthesis of Enantiopure 2-C-Methyl-d-erythritol 4-Phosphate and 2,4-Cyclodiphosphate from d-Arabitol

Two key intermediates of the newly discovered mevalonate-independent pathway for isoprenoid biosynthesis were prepared. Optically pure 2-C-methyl-d-erythritol 4-phosphate and 2,4-cyclodiphosphate were chemically synthesized from d-arabitol using a convenient benzylidene and tert-butyldimethylsilyl p...

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Veröffentlicht in:Organic letters 2004-01, Vol.6 (1), p.135-138
Hauptverfasser: Urbansky, Marek, Davis, Chad E, Surjan, Jacob D, Coates, Robert M
Format: Artikel
Sprache:eng
Schlagworte:
Erythritol - analogs & derivatives
Erythritol - chemical synthesis
Models, Chemical
Stereoisomerism
Sugar Alcohols - chemical synthesis
Sugar Alcohols - chemistry
Sugar Phosphates - chemical synthesis
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Zusammenfassung:Two key intermediates of the newly discovered mevalonate-independent pathway for isoprenoid biosynthesis were prepared. Optically pure 2-C-methyl-d-erythritol 4-phosphate and 2,4-cyclodiphosphate were chemically synthesized from d-arabitol using a convenient benzylidene and tert-butyldimethylsilyl protection of polyhydroxylated intermediates. The new scheme offers a straightforward route to analogues and labeled forms.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0362562