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Synthesis 2004(11): 1844-1848  
DOI: 10.1055/s-2004-829139
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© Georg Thieme Verlag Stuttgart · New York

Synthesis of Virgatol and Virgatenol, Two Naturally Occurring Coumarins from Pterocaulon virgatum (L.) DC, and 7-(2,3-Epoxy-3-methylbutoxy)-6-methoxycoumarin­, Isolated from Conyza obscura DC

Jan Demyttenaerea, Stijn Vervischa, Silvia Debenedettib, Jorge Coussioc, Dominick Maesa, Norbert De Kimpe*a
a Department of Organic Chemistry, Faculty of Agricultural and Applied Biological Sciences, Ghent University, Coupure links 653, 9000 Ghent, Belgium
Fax: +32(9)2646243; e-Mail: norbert.dekimpe@ugent.be;
b Department of Biological Sciences, University of La Plata, Calle 115 and 47, 1900 La Plata, Argentina
c IQUIMEFA, Faculty of Pharmacy, University of Buenos Aires, Junin 956, 1113 Buenos Aires, Argentina
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Publication History

Received 4 December 2003
Publication Date:
13 July 2004 (online)

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Abstract

The synthesis of a number of naturally occurring coumarins from Pterocaulon virgatum (L.) and Conyza obscura DC is described for the first time. It concerns the synthesis of 7-(2-hydroxy-3-methoxy-3-methylbutoxy)-6-methoxycoumarin (virgatol, 1), 7-(2-hydroxy-3-methyl-3-butenyloxy)-6-methoxycoumarin (virgatenol, 2) and 7-(2,3-epoxy-3-methylbutoxy)-6-methoxycoumarin (3). In addition, a straightforward synthesis of scopoletin (4) (7-hydroxy-6-methoxycoumarin) is reported and the synthesis of a new coumarin derivative, 6-methoxy-7-(2-oxo-3-methylbutoxy)coumarin (7), is described.

Keywords

virgatol - virgatenol - coumarins - natural products - Wittig reactions - epoxides