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 Demyttenaere; Stijn Vervisch; Silvia Debenedetti; Jorge Coussio; Dominick Maes; Norbert De Kimpe

doi:10.1055/s-2004-829139

PAPER

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 Demyttenaere^a, Stijn Vervisch^a, Silvia Debenedetti^b, Jorge Coussio^c, Dominick Maes^a, 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

Abstract

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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

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Referenzen

References

1 Murray RDH. Méndez J. Brown RA. The Natural Coumarins Wiley; New York: 1982.

2 Murray RDH. Nat. Prod. Rep. 1989, 8: 591

3 Murray RDH. In Progress in the Chemistry of Organic Natural Products Vol. 58: Springer-Verlag; Vienna, New York: 1991. p.83

4 Murray RDH. In Progress in the Chemistry of Organic Natural Products Vol. 72: Springer-Verlag; Vienna, New York: 1997. p.2

5 Hoult JRS. Payá M. Gen. Pharmac. 1996, 27: 713

6 Egan D. O’Kennedy R. Moran E. Cox C. Prosser E. Thornes RD. Drug Metab. Rev. 1990, 22: 503

7 Laurin P. Klich M. Dupis-Hamelin C. Mauvais P. Lassaigne P. Bonnefoy A. Musicki B. Bioorg. Med. Chem. Lett. 1999, 9: 2079

8 Pillai SP. Menon SR. Mitscher LA. Pillai CA. Shankel DA. J. Nat. Prod. 1999, 62: 1358

9 Noguchi M. Earashi M. Minami M. Miyazaki I. Tanaka M. Sasaki T. Prostaglandins Leukot. Essent. Fatty Acids 1995, 53: 325

10 Kawaii S. Tomono Y. Ogawa K. Sugiura M. Yano M. Yoshizawa Y. Anticancer Res. 2001, 21: 917

11 Chimichi S. Boccalini M. Cosimelli B. Viola G. Vedaldi D. Dall"Acqua F. Tetrahedron Lett. 2002, 43: 7473

12 Jimenez-Orozco FA. Molina-Guarneros JA. Mendoza-Patino N. Leon-Cedeno F. Flores-Perez B. Santos-Santos E. Mandoki JJ. Melanoma Res. 1999, 9: 243

13 Hofmanova J. Kozubik A. Kusek L. Pachemik J. Eur. J. Pharmacol. 1998, 350: 273

14 Roma G. Braccio MD. Carrieri A. Grossi G. Leoncini G. Grazia-Signorello M. Carotti A. Bioorg. Med. Chem. 2003, 11: 123

15 Kirkiacharian S. Thuy DT. Sicsic S. Bakhchinian R. Kurkjian R. Tonnaire T. Farmaco 2002, 57: 703

16 Seliger B. In Coumarins: Biology, Applications and Mode of Action O’Kennedy R. Thornes RD. Wiley; New York: 1997. p.93

17 Debenedetti S. Nadinic EL. Coussio JD. De Kimpe N. Boeykens M. Phytochemistry 1998, 48: 707

18 Palacios RS. Rojo AA. Coussio JD. De Kimpe N. Debenedetti SL. Planta Medica 1999, 65: 294

19 Bohlmann F. Jakupovic J. Phytochemistry 1979, 18: 1367

20 Debenedetti SL. De Kimpe N. Boeykens M. Coussio JD. Kesteleyn B. Phytochemistry 1997, 45: 1515

21 Debenedetti SL. Nadinic EL. Gomez MA. Coussio JD. De Kimpe N. Boeykens M. Phytochemistry 1996, 42: 563

22 Riviero ME. Shayo C. Monczor F. Fernandez N. Baldi A. De Kimpe N. Rossi J. Debenedetti SL. Davio C. Cancer Lett. 2004, 210: 178

23 Seka R. Kallir P. Ber. Dtsch. Chem. Ges. 1931, 64: 909

24 Head FSH. Robertson A. J. Chem Soc. 1931, 1241

25 Ahluwa1ia VK. Khanna NH. Singh RP. Monatsh. Chem. 1982, 113: 197

26 Crosby DG. J. Org. Chem. 1961, 26: 1215

27 Moore CW. J. Chem. Soc. 1911, 1043

28 Demyttenaere J. Van Syngel K. Markusse AP. Vervisch S. Debenedetti S. De Kimpe N. Tetrahedron 2002, 58: 2163

29 Ishi H. Ishikawa T. Wada H. Miyazaki H. Kaneko Y. Harayama T. Chem. Pharm. Bull. 1992, 40: 2614

30 Ballantyne MM. Murray RDH. Penrose AB. Tetrahedron Lett. 1968, 9: 4155

31 Ballantyne MM. McCabe PH. Murray RDH. Tetrahedron 1971, 27: 871

32 Cardona L. García B. Pedro JR. Pérez J. Phytochemistry 1992, 31: 3989

34 Herz W. Bhat SV. Santhanam PS. Phytochemistry 1970, 9: 891

35 Zdero C. Bohlmann F. Niemeyer HM. Phytochemistry 1990, 29: 326

36 Pistelli L. Bertoli A. Bilia AR. Morelli I. Phytochemistry 1996, 41: 1579

37 Schultez AG. Nombres Comunes de las Plantas Subsecretary of Culture of Province of Chaco; Chaco: 1976. p.225

38 Soraru B. Bandoni A. Plantas de la Medicina Popular Argentina Albatros; Buenos Aires: 1978. p.41

39 Arenas P. Etnobotanica Lengua Maskoy FECYC; Buenos Aires: 1981. p.332

40 Boelke O. Plantas Vasculares de la Argentina, Nativas y Exoticas FECYC; Buenos Aires: 1981. p.265

41 Villa MJ. Warren S. J. Chem. Soc. Perkin Trans. 1 1994, 1569

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

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