Synthesis of a C(4)-C(9) eleutheside template from D-glucal

Kolbot By, Patrick A. Kelly, Mark J. Kurth, Marilyn M. Olmstead, Michael H. Nantz

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

D-Glucal is converted to epoxy allylic alcohol 4 using an eight-step sequence that features a stereoselective methyl Grignard addition to an iodo-hexenulose. Epoxide formation via intramolecular iodide displacement occurs subsequent to an unusual hemiacetal reduction protocol involving LiBH4 in n-octanol. Alcohol 4 and the corresponding aldehyde (Z)-14 are potential C(4)-C(9) templates for eleutheside syntheses.

Original languageEnglish (US)
Pages (from-to)1183-1187
Number of pages5
JournalTetrahedron
Volume57
Issue number7
DOIs
StatePublished - Feb 11 2001

Keywords

  • D-glucal
  • Eleutheside
  • Epoxide
  • Hexenulose
  • Stereoselective

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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