Catalytic asymmetric synthesis of a 1-deoxy-1,1-difluoro-D-xylulose

Liam R Cox, Gareth A DeBoos, Jeremy J Fullbrook, Jonathan Percy, Neil S Spencer, Malcolm Tolley

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

A new route, of potential strategic importance, to a difluorosugar analogue has been developed. Key steps included a Stille coupling and a highly regio- and enantioselective dihydroxylation of a highly substituted diene. Protecting groups were chosen to enhance the reactivity of the disubstituted allylic fragment in the AD reaction and allow deprotection under orthogonal conditions.
LanguageEnglish
Pages337-339
Number of pages3
JournalOrganic Letters
Volume5
Issue number3
DOIs
Publication statusPublished - 6 Feb 2003

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dienes
reactivity
routes
fragments
analogs
synthesis
1-deoxy-1,1-difluoro-D-xylulose

Keywords

  • catalytic sysnthesis
  • Stille coupling
  • orthogonal conditions

Cite this

Cox, L. R., DeBoos, G. A., Fullbrook, J. J., Percy, J., Spencer, N. S., & Tolley, M. (2003). Catalytic asymmetric synthesis of a 1-deoxy-1,1-difluoro-D-xylulose. Organic Letters, 5(3), 337-339 . https://doi.org/10.1021/ol02735
Cox, Liam R ; DeBoos, Gareth A ; Fullbrook, Jeremy J ; Percy, Jonathan ; Spencer, Neil S ; Tolley, Malcolm. / Catalytic asymmetric synthesis of a 1-deoxy-1,1-difluoro-D-xylulose. In: Organic Letters. 2003 ; Vol. 5, No. 3. pp. 337-339 .
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Cox, LR, DeBoos, GA, Fullbrook, JJ, Percy, J, Spencer, NS & Tolley, M 2003, 'Catalytic asymmetric synthesis of a 1-deoxy-1,1-difluoro-D-xylulose' Organic Letters, vol. 5, no. 3, pp. 337-339 . https://doi.org/10.1021/ol02735

Catalytic asymmetric synthesis of a 1-deoxy-1,1-difluoro-D-xylulose. / Cox, Liam R; DeBoos, Gareth A; Fullbrook, Jeremy J; Percy, Jonathan; Spencer, Neil S; Tolley, Malcolm.

In: Organic Letters, Vol. 5, No. 3, 06.02.2003, p. 337-339 .

Research output: Contribution to journalArticle

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Cox LR, DeBoos GA, Fullbrook JJ, Percy J, Spencer NS, Tolley M. Catalytic asymmetric synthesis of a 1-deoxy-1,1-difluoro-D-xylulose. Organic Letters. 2003 Feb 6;5(3):337-339 . https://doi.org/10.1021/ol02735