NON-CONVENTIONAL EPIMERISATION AND FUNCTIONALISATION OF QUINIC ACID AND SHIKIMIC ACID METHYL ESTERS
作者： Michael Frank , Ralf Miethchen
DOI: 10.1016/S0008-6215(98)00220-1
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摘要: Abstract In a convenient one-pot acetalation procedure using chloral/DCC, methyl (-)-quinate and (-)-shikimate were converted into their 4- epi -derivatives containing carbamoyl function in 3-position the trichloroethylidene acetal group 4,5-position. Additionally, an spiro-byproduct, 1 R, 3 4 5 R)- ′-N- cyclohexyl - -O-( cyclohexylcarbomyl )- 4,5 2,2,2-trichloroethylidene)spiro[[cyclohexane-3,4,5-triol-1,5′-[1,3]oxazolidine]]-2′,4′-dione , was formed from 10% yield. Decarbamoylation of compounds is possible by heating methanolic sodium methoxide.
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