Two-step synthesis of carbohydrates by selective aldol reactions

Alan B. Northrup, David W.C. MacMillan

Research output: Contribution to journalArticle

325 Scopus citations

Abstract

Studies of carbohydrates have been hampered by the lack of chemical strategies for the expeditious construction and coupling of differentially protected monosaccharides. Here, a synthetic route based on aldol coupling of three aldehydes is presented for the de novo production of polyol differentiated hexoses in only two chemical steps. The dimerization of α-oxyaldehydes, catalyzed by L-proline, is then followed by a tandem Mukaiyama aldol addition-cyclization step catalyzed by a Lewis acid. Differentially protected glucose, allose, and mannose stereoisomers can each be selected, in high yield and stereochemical purity, simply by changing the solvent and Lewis acid used. The reaction sequence also efficiently produces 13C-labeled analogs, as well as structural variants such as 2-amino- and 2-thio-substituted derivatives.

Original languageEnglish (US)
Pages (from-to)1752-1755
Number of pages4
JournalScience
Volume305
Issue number5691
DOIs
StatePublished - Sep 17 2004

All Science Journal Classification (ASJC) codes

  • General

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