-)-Quinic acid in organic synthesis. 1. A facile synthesis of 2- crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone

Tony K.M. Shing, Ying Tang

Research output: Contribution to journalArticle

54 Citations (Scopus)

Abstract

The glyoxalase 1 inhibitor COTC (2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (1) has been synthesised from (-)-quinic acid in thirteen steps; an interesting rearrangement involving a silyl migration upon oxidation of (l10) is also described.

Original languageEnglish
Pages (from-to)6575-6584
Number of pages10
JournalTetrahedron
Volume46
Issue number18
DOIs
Publication statusPublished - 1990

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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