Synthesis of Chloramphenicol via a new Intermediate 4-<i>para</i>-Nitrophenyl-5-formamido-1,3-dioxane
作者:Braja G Hazra、Vandana S. Pore、Shailaja P. Maybhate
DOI:10.1080/00397919708006786
日期:1997.6
Abstract 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.
摘要 4-苯基-5-氨基-1,3-二恶烷 4,从 β-溴苯乙烯 2 得到保护为甲酰胺衍生物 5。5 的硝化,然后区域选择性酰化裂解硝基产物 12 得到 N-甲酰基-N-乙酰半缩醛二乙酸酯 16,在依次碱水解和酸水解,然后二氯乙酰化后得到氯霉素 1。