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 journalArticle

12 Citations (Scopus)

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

Fingerprint

1-Octanol
Calcium Gluconate
Epoxy Compounds
Iodides
Aldehydes
Alcohols
allyl alcohol

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

By, K., Kelly, P. A., Kurth, M. J., Olmstead, M. M., & Nantz, M. H. (2001). Synthesis of a C(4)-C(9) eleutheside template from D-glucal. Tetrahedron, 57(7), 1183-1187. https://doi.org/10.1016/S0040-4020(00)01117-0

Synthesis of a C(4)-C(9) eleutheside template from D-glucal. / By, Kolbot; Kelly, Patrick A.; Kurth, Mark J.; Olmstead, Marilyn M.; Nantz, Michael H.

In: Tetrahedron, Vol. 57, No. 7, 11.02.2001, p. 1183-1187.

Research output: Contribution to journalArticle

By, K, Kelly, PA, Kurth, MJ, Olmstead, MM & Nantz, MH 2001, 'Synthesis of a C(4)-C(9) eleutheside template from D-glucal', Tetrahedron, vol. 57, no. 7, pp. 1183-1187. https://doi.org/10.1016/S0040-4020(00)01117-0
By K, Kelly PA, Kurth MJ, Olmstead MM, Nantz MH. Synthesis of a C(4)-C(9) eleutheside template from D-glucal. Tetrahedron. 2001 Feb 11;57(7):1183-1187. https://doi.org/10.1016/S0040-4020(00)01117-0
By, Kolbot ; Kelly, Patrick A. ; Kurth, Mark J. ; Olmstead, Marilyn M. ; Nantz, Michael H. / Synthesis of a C(4)-C(9) eleutheside template from D-glucal. In: Tetrahedron. 2001 ; Vol. 57, No. 7. pp. 1183-1187.
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