Intramolecular aldol condensation applied to d-glucose-derived δ-ketoaldehydes: access to enantiomerically pure six-membered carbocycles

Kin ichi Tadano, Satoshi Kanazawa, Ken ichi Takao, Seiichiro Ogawa

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

An enantiomerically pure δ-ketoaldehyde 10, efficiently prepared from D-glucose, was subjected to an intramolecular aldol condensation. By using DBU as a base, the expecting aldol reaction took place smoothly giving the aldol 11 stereoselectively. Further functionalization of 11 provided tri-C-substituted cyclohexanediols 26 and 27, via the functionalized cyclohexenone15.

Original languageEnglish
Pages (from-to)4283-4300
Number of pages18
JournalTetrahedron
Volume48
Issue number21
DOIs
Publication statusPublished - 1992

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Keywords

  • D-glucose-derived δ-ketoaldehyde
  • intramolecular aldol condensation
  • tri-C-alkylated cyclohexanoids

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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