Reinvestigation of the synthesis of (2R,3R) 2,3-(cyclohexylidenedioxy)-4-cyclopentenone as possible building block for the synthesis of carbocyclic nucleosides

Article abstract of DOI:10.1080/00397919708005020

An in depth study of the four-steps synthesis of (2R,3R) 2,3-(cyclohexylidenedioxy)-4-cyclopentenone (5) from D-ribonolactone (1) is described. From these experiments we must conclude that the overall yield reported in the literature (65%) is overestimated. All compounds have been throughly investigated by ¹H- and ¹³C-NMR spectroscopy.

Full text of DOI:10.1080/00397919708005020

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Synthetic Communications: An
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Reinvestigation of the
Synthesis of (2R,3R) 2,3-
(Cyclohexylidenedioxy)-4-
cyclopentenone as Possible
Building Block for the Synthesis
of Carbocyclic Nucleosides.
C. L. Mariën a , E. L. Esmans a , F. Lemière a & R. A.
Dommisse a
a University of Antwerp (RUCA), Department
of Chemistry, Nucleoside Research & Mass
Spectrometry Unit , Groenenborgerlaan 171, B-2020,
Antwerp, BELGIUM
Published online: 22 Aug 2006.
To cite this article: C. L. Mariën , E. L. Esmans , F. Lemière & R. A. Dommisse
(1997) Reinvestigation of the Synthesis of (2R,3R) 2,3-(Cyclohexylidenedioxy)-4-
cyclopentenone as Possible Building Block for the Synthesis of Carbocyclic
Nucleosides., Synthetic Communications: An International Journal for Rapid
Communication of Synthetic Organic Chemistry, 27:2, 205-224
To link to this article: http://dx.doi.org/10.1080/00397919708005020
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