Synthesis of chloramphenicol via a new intermediate 4-para-nitrophenyl- 5-formamido-1,3-dioxane

Article abstract of DOI:10.1080/00397919708006786

4-Phenyl-5-amino-1,3-dioxane 4, obtained from β-bromo styrene 2 was protected as formamido derivative 5. Nitration of 5 followed by regioselective acylative cleavage of the nitro product 12 gave N-formyl-N- acetyl hemiacetal diacetate 16, which on sequential base and acid hydrolysis followed by dichloroacetylation gave chloramphenicol 1.

Full text of DOI:10.1080/00397919708006786

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Synthetic Communications: An
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Synthesis of Chloramphenicol
via a new Intermediate 4-para-
Nitrophenyl-5-formamido-1,3-
dioxane
Braja G Hazra a , Vandana S. Pore a & Shailaja P.
Maybhate a
a Division of Organic Chemistry (Synthesis), National
Chemical Laboratory, Pune, 411008, India
Available online: 22 Aug 2006
To cite this article: Braja G Hazra, Vandana S. Pore & Shailaja P. Maybhate (1997):
Synthesis of Chloramphenicol via a new Intermediate 4-para-Nitrophenyl-5-
formamido-1,3-dioxane, Synthetic Communications: An International Journal for
Rapid Communication of Synthetic Organic Chemistry, 27:11, 1857-1864
To link to this article: http://dx.doi.org/10.1080/00397919708006786
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