Synthetic studies towards (-)-carba-3′-deoxy-3′-fluorothymidine.

J. Béres, Gy Sági, E. Baitz-Gács, I. Tömösközi, L. Gruber, L. Ötvös

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Stereospecific synthesis of (-)-carba-3′-deoxy-3′-fluorothymidine (-)-11 is reported from the protected (-)-carbocyclic 3′-epi-thymidine (-)-7 using diethylaminosulfur trifluoride. Under the conditions used, extensive dehydration of the blocked precursor into 10 and formation of the 4′-fluoro analogue (9) were also observed. An attempted simplification of our methodology based on (+)-(1R, 5S)-2-oxabicyclo[3.3.0]oct-6-en-3-one failed, but a novel cyclopentane (2) ring expansion to tetrahydropyran (18) was discovered.

Original languageEnglish
Pages (from-to)6271-6280
Number of pages10
JournalTetrahedron
Volume45
Issue number19
DOIs
Publication statusPublished - 1989

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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    Béres, J., Sági, G., Baitz-Gács, E., Tömösközi, I., Gruber, L., & Ötvös, L. (1989). Synthetic studies towards (-)-carba-3′-deoxy-3′-fluorothymidine. Tetrahedron, 45(19), 6271-6280. https://doi.org/10.1016/S0040-4020(01)85137-1