Synthesis of 1D-3-deoxy- and -2,3-dideoxyphosphatidylinositol

Alan P. Kozikowski, Lixin Qiao, Werner Tückmantel, Garth Powis

Research output: Contribution to journalArticle

Abstract

Both 1D-3-deoxy- and -2,3-dideoxyphosphatidylinositol (3 and 18) were synthesized using the regioisomeric mixture of viburnitol 1,2:4,5- and 1,2:5,6- diacetonides as starting material. Selective acidic hydrolysis and subsequent benzylation or deoxygenation afforded 11a,b as important intermediates. Compound 3 and 18 were of interest as putative antimetabolites of phosphatidylinositol-3-phosphate and as inhibitors of cancer cell colony formation.

Original languageEnglish (US)
Pages (from-to)14903-14914
Number of pages12
JournalTetrahedron
Volume53
Issue number44
DOIs
StatePublished - Nov 3 1997
Externally publishedYes

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Antimetabolites
Hydrolysis
Cells
Neoplasms
phosphatidylinositol 3-phosphate
compound 18

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Kozikowski, A. P., Qiao, L., Tückmantel, W., & Powis, G. (1997). Synthesis of 1D-3-deoxy- and -2,3-dideoxyphosphatidylinositol. Tetrahedron, 53(44), 14903-14914. https://doi.org/10.1016/S0040-4020(97)10003-5

Synthesis of 1D-3-deoxy- and -2,3-dideoxyphosphatidylinositol. / Kozikowski, Alan P.; Qiao, Lixin; Tückmantel, Werner; Powis, Garth.

In: Tetrahedron, Vol. 53, No. 44, 03.11.1997, p. 14903-14914.

Research output: Contribution to journalArticle

Kozikowski, AP, Qiao, L, Tückmantel, W & Powis, G 1997, 'Synthesis of 1D-3-deoxy- and -2,3-dideoxyphosphatidylinositol', Tetrahedron, vol. 53, no. 44, pp. 14903-14914. https://doi.org/10.1016/S0040-4020(97)10003-5
Kozikowski AP, Qiao L, Tückmantel W, Powis G. Synthesis of 1D-3-deoxy- and -2,3-dideoxyphosphatidylinositol. Tetrahedron. 1997 Nov 3;53(44):14903-14914. https://doi.org/10.1016/S0040-4020(97)10003-5
Kozikowski, Alan P. ; Qiao, Lixin ; Tückmantel, Werner ; Powis, Garth. / Synthesis of 1D-3-deoxy- and -2,3-dideoxyphosphatidylinositol. In: Tetrahedron. 1997 ; Vol. 53, No. 44. pp. 14903-14914.
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