Stereospecific synthesis of (+) -cahbocyclic 2'-deoxyadenosine. an improved procedure for the preparation of (+)-(1r,2s,4r)-4-amino-2-hydroxy-1-hydroxymethylcyclopentane.

J. Béres, Gy Sági, E. Baitz-Gács, I. Töaöaközi, L. Ötivös

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Abstract

An improved procedure for the preparation of a versatile synthetic precursor, (+)-13, of carba-2'-deoxyribonucleosides and the first stereospecific way to enantiomerically pure carbocyclic 2'-deoxyadenosine, (+)-14, are presented from bicyclic lactone diol (+)-1. An unexpected formation of the disubstituted 2-oxabicyclo[2.2.1]heptane skeleton 15 through a hypervalent iodo species derived from 6 is also reported.

Original languageEnglish
Pages (from-to)6207-6216
Number of pages10
JournalTetrahedron
Volume44
Issue number19
DOIs
Publication statusPublished - 1988

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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