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
References
<A NAME="RT13103SS-1">1 </A>
Murray RDH.
Méndez J.
Brown RA.
The Natural Coumarins
Wiley;
New York:
1982.
<A NAME="RT13103SS-2">2 </A>
Murray RDH.
Nat. Prod. Rep.
1989,
8:
591
<A NAME="RT13103SS-3">3 </A>
Murray RDH. In
Progress in the Chemistry of Organic Natural Products
Vol. 58:
Springer-Verlag;
Vienna, New York:
1991.
p.83
<A NAME="RT13103SS-4">4 </A>
Murray RDH. In
Progress in the Chemistry of Organic Natural Products
Vol. 72:
Springer-Verlag;
Vienna, New York:
1997.
p.2
<A NAME="RT13103SS-5">5 </A>
Hoult JRS.
Payá M.
Gen. Pharmac.
1996,
27:
713
<A NAME="RT13103SS-6">6 </A>
Egan D.
O’Kennedy R.
Moran E.
Cox C.
Prosser E.
Thornes RD.
Drug Metab. Rev.
1990,
22:
503
<A NAME="RT13103SS-7">7 </A>
Laurin P.
Klich M.
Dupis-Hamelin C.
Mauvais P.
Lassaigne P.
Bonnefoy A.
Musicki B.
Bioorg. Med. Chem. Lett.
1999,
9:
2079
<A NAME="RT13103SS-8">8 </A>
Pillai SP.
Menon SR.
Mitscher LA.
Pillai CA.
Shankel DA.
J. Nat. Prod.
1999,
62:
1358
<A NAME="RT13103SS-9">9 </A>
Noguchi M.
Earashi M.
Minami M.
Miyazaki I.
Tanaka M.
Sasaki T.
Prostaglandins Leukot. Essent. Fatty Acids
1995,
53:
325
<A NAME="RT13103SS-10">10 </A>
Kawaii S.
Tomono Y.
Ogawa K.
Sugiura M.
Yano M.
Yoshizawa Y.
Anticancer Res.
2001,
21:
917
<A NAME="RT13103SS-11">11 </A>
Chimichi S.
Boccalini M.
Cosimelli B.
Viola G.
Vedaldi D.
Dall"Acqua F.
Tetrahedron Lett.
2002,
43:
7473
<A NAME="RT13103SS-12">12 </A>
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
<A NAME="RT13103SS-13">13 </A>
Hofmanova J.
Kozubik A.
Kusek L.
Pachemik J.
Eur. J. Pharmacol.
1998,
350:
273
<A NAME="RT13103SS-14">14 </A>
Roma G.
Braccio MD.
Carrieri A.
Grossi G.
Leoncini G.
Grazia-Signorello M.
Carotti A.
Bioorg. Med. Chem.
2003,
11:
123
<A NAME="RT13103SS-15">15 </A>
Kirkiacharian S.
Thuy DT.
Sicsic S.
Bakhchinian R.
Kurkjian R.
Tonnaire T.
Farmaco
2002,
57:
703
<A NAME="RT13103SS-16">16 </A>
Seliger B. In
Coumarins: Biology, Applications and Mode of Action
O’Kennedy R.
Thornes RD.
Wiley;
New York:
1997.
p.93
<A NAME="RT13103SS-17">17 </A>
Debenedetti S.
Nadinic EL.
Coussio JD.
De Kimpe N.
Boeykens M.
Phytochemistry
1998,
48:
707
<A NAME="RT13103SS-18">18 </A>
Palacios RS.
Rojo AA.
Coussio JD.
De Kimpe N.
Debenedetti SL.
Planta Medica
1999,
65:
294
<A NAME="RT13103SS-19">19 </A>
Bohlmann F.
Jakupovic J.
Phytochemistry
1979,
18:
1367
<A NAME="RT13103SS-20">20 </A>
Debenedetti SL.
De Kimpe N.
Boeykens M.
Coussio JD.
Kesteleyn B.
Phytochemistry
1997,
45:
1515
<A NAME="RT13103SS-21">21 </A>
Debenedetti SL.
Nadinic EL.
Gomez MA.
Coussio JD.
De Kimpe N.
Boeykens M.
Phytochemistry
1996,
42:
563
<A NAME="RT13103SS-22">22 </A>
Riviero ME.
Shayo C.
Monczor F.
Fernandez N.
Baldi A.
De Kimpe N.
Rossi J.
Debenedetti SL.
Davio C.
Cancer Lett.
2004,
210:
178
<A NAME="RT13103SS-23">23 </A>
Seka R.
Kallir P.
Ber. Dtsch. Chem. Ges.
1931,
64:
909
<A NAME="RT13103SS-24">24 </A>
Head FSH.
Robertson A.
J. Chem Soc.
1931,
1241
<A NAME="RT13103SS-25">25 </A>
Ahluwa1ia VK.
Khanna NH.
Singh RP.
Monatsh. Chem.
1982,
113:
197
<A NAME="RT13103SS-26">26 </A>
Crosby DG.
J. Org. Chem.
1961,
26:
1215
<A NAME="RT13103SS-27">27 </A>
Moore CW.
J. Chem. Soc.
1911,
1043
<A NAME="RT13103SS-28">28 </A>
Demyttenaere J.
Van Syngel K.
Markusse AP.
Vervisch S.
Debenedetti S.
De Kimpe N.
Tetrahedron
2002,
58:
2163
<A NAME="RT13103SS-29">29 </A>
Ishi H.
Ishikawa T.
Wada H.
Miyazaki H.
Kaneko Y.
Harayama T.
Chem. Pharm. Bull.
1992,
40:
2614
<A NAME="RT13103SS-30">30 </A>
Ballantyne MM.
Murray RDH.
Penrose AB.
Tetrahedron Lett.
1968,
9:
4155
<A NAME="RT13103SS-31">31 </A>
Ballantyne MM.
McCabe PH.
Murray RDH.
Tetrahedron
1971,
27:
871
<A NAME="RT13103SS-32">32 </A>
Cardona L.
García B.
Pedro JR.
Pérez J.
Phytochemistry
1992,
31:
3989
<A NAME="RT13103SS-33">33 </A>
McCabe PH.
McCrindle R.
Murray RDH.
J. Chem. Soc. (C)
1967,
145
<A NAME="RT13103SS-34">34 </A>
Herz W.
Bhat SV.
Santhanam PS.
Phytochemistry
1970,
9:
891
<A NAME="RT13103SS-35">35 </A>
Zdero C.
Bohlmann F.
Niemeyer HM.
Phytochemistry
1990,
29:
326
<A NAME="RT13103SS-36">36 </A>
Pistelli L.
Bertoli A.
Bilia AR.
Morelli I.
Phytochemistry
1996,
41:
1579
<A NAME="RT13103SS-37">37 </A>
Schultez AG.
Nombres Comunes de las Plantas
Subsecretary of Culture of Province of Chaco;
Chaco:
1976.
p.225
<A NAME="RT13103SS-38">38 </A>
Soraru B.
Bandoni A.
Plantas de la Medicina Popular Argentina
Albatros;
Buenos Aires:
1978.
p.41
<A NAME="RT13103SS-39">39 </A>
Arenas P.
Etnobotanica Lengua Maskoy
FECYC;
Buenos Aires:
1981.
p.332
<A NAME="RT13103SS-40">40 </A>
Boelke O.
Plantas Vasculares de la Argentina, Nativas y Exoticas
FECYC;
Buenos Aires:
1981.
p.265
<A NAME="RT13103SS-41">41 </A>
Villa MJ.
Warren S.
J. Chem. Soc. Perkin Trans. 1
1994,
1569
