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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 10
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Original Articles

Simple and Convenient Synthesis of 4‐Unsubstituted‐3‐(3‐Oxoalkyl)isocoumarins

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Pages 1569-1578 | Received 02 Oct 2007, Published online: 24 Apr 2008

References

  • Barry , R. D. 1964 . Isocoumarins: Developments since 1950 . Chem. Rev. , 64 : 229 – 260 .
  • Eaton , M. A. W. and Hutchinson , D. W. 1971 . Isocoumarins from Streptomyces mobaraensis . Tetrahedron Lett. , 12 : 1337 – 1340 .
  • McGraw , G. W. and Hemingway , R. W. 1977 . 6,8‐Dihydroxy‐3‐hydroxymethylisocoumarin, and other phenolic metabolites of Ceratocystis minor . Phytochemistry , 16 : 1315 – 1316 .
  • Ellestad , G. A. , Lovell , F. M. , Perkinson , N. A. , Hargreaves , R. T. and McGahren , W. J. 1978 . New zearalenone related macrolides and isocoumarins from an unidentified fungus . J. Org. Chem. , 43 : 2339 – 2343 .
  • Lai , S. , Shizuri , Y. , Yamamura , S. , Kawai , K. and Furukawa , H. 1991 . Three new phenolic metabolites from Penicillium species . Heterocycles , 32 : 297 – 305 .
  • Watanabe , A. , Ono , Y. , Fujii , I. , Sankawa , U. , Mayorga , M. E. , Timberlake , W. E. and Ebizuka , Y. 1998 . Product identification of polyketide synthase coded by Aspergillus nidulans wA gene . Tetrahedron Lett. , 39 : 7733 – 7736 .
  • Larsen , T. O. and Breinholt , J. 1999 . Dichlorodiaportin, diaportinol, and diaportinic acid: Three novel isocoumarins from Penicillium nalgiovense . J. Nat. Prod. , 62 : 1182 – 1184 .
  • Harris , J. P. and Mantle , P. G. 2001 . Biosynthesis of diaporthin and orthosporin by Aspergillus ochraceus . Phytochemistry , 57 : 165 – 169 .
  • Quang , D. N. , Hashimoto , T. , Tanaka , M. , Baumgartner , M. , Stadler , M. and Asakawa , Y. 2002 . Chemical constituents of the ascomycete Daldinia concentrica. . J. Nat. Prod. , 65 : 1869 – 1874 .
  • Tanahashi , T. , Takenaka , Y. , Nagakura , N. , Hamada , N. and Miyawaki , H. 2000 . Two isocoumarins from the cultured lichen mycobiont of Graphis sp . Heterocycles , 53 : 723 – 728 .
  • Harada , R. , Noguchi , S. and Sugiyama , N. 1960 . Essential oil of Artemisia capillaris, VI: The structure of capillarin . Nippon Kagaku Zasshi , 81 : 654 – 658 . Chem. Abstr. 1961, 55, 8398
  • Bohlmann , F. and Zdero , C. 1970 . Polyacetylenverbindungen, 184: Die Inhaltsstoffe aus Anthemis fuscata Brot . Chem. Ber. , 103 : 2856 – 2859 .
  • Bohlmann , F. and Zdero , C. 1976 . Neue inhaltsstoffe aus Felicia‐Arten . Phytochemistry , 15 : 1318 – 1319 .
  • Gregr , H. 1979 . Aromatic acetylenes and dehydrofalcarinone derivatives within the Artemisia dracunculus group . Phytochemistry , 18 : 1319 – 1322 .
  • Stepanenko , L. S. , Krivoshchekova , O. E. and Mishchenko , N. P. 1985 . Chemical variations of Asahinea chrysantha . Phytochemistry , 24 : 354 – 355 .
  • Ruangrungsi , N. , Sekine , T. , Phadungcharoen , T. , Suriyagan , S. and Murakoshi , I. 1995 . Isocoumarins from Xyris indica . Phytochemistry , 38 : 481 – 483 .
  • Meepagala , K. , Sturtz , G. and Wedge , D. E. 2002 . Antifungal constituents of the essential oil fraction of Artemisia dracunculus L. var . Dracunculus. J. Agric. Food Chem. , 50 : 6989 – 6992 .
  • Ichihara , A. , Hashimoto , M. , Hirai , T. , Takeda , I. , Sasamura , Y. , Sakamura , S. , Sato , R. and Tajimi , A. 1989 . Structure, synthesis, and stereochemistry of (+)‐orthosporin, a phytotoxic metabolite of Rynchosporium orthosporum . Chem. Lett. , : 1495 – 1498 .
  • Lutz‐Kutschera , G. , Engelmeier , D. , Hadacek , F. , Werner , A. , Greger , H. and Hofer , O. 2003 . Synthesis of side chain substituted 3‐butylisocoumarins and absolute configurations of natural isocoumarins from Artemisia dracunculus . Monatsh. Chem. , 134 : 1195 – 1206 .
  • Engelmeier , D. , Hadacek , F. , Hofer , O. , Lutz‐Kutschera , G. , Nagl , M. , Wurz , G. and Greger , H. 2004 . Antifungal 3‐butylisocoumarins from asteraceae‐anthemideae . J. Nat Prod. , 67 : 19 – 25 . and references therein
  • Rama , N. H. , Iqbal , R. , Zamani , K. , Saeed , A. , Iqbal , M. Z. and Chaudary , M. I. 1998 . Synthesis and anti‐bacterial activity of some 3‐alkylisocoumarins and (±)‐3‐alkyl‐3,4‐ dihydroisocoumarins . Indian J. Chem. , 37B : 365 – 369 .
  • Kumagai , H. , Masuda , T. , Ohsono , M. , Hattori , S. , Naganawa , H. , Sawa , T. , Hamada , M. , Ishizuka , M. and Takeuchi , T. 1990 . Cytogenin, a novel antitumor substance . J. Antibiotics , 43 : 1505 – 1507 .
  • Kumagai , H. , Masuda , T. , Ishizuka , M. and Takeuchi , T. 1995 . Antitumor activity of cytogenin . J. Antibiotics , 48 : 175 – 178 .
  • Salloum , R. M. , Jaskowiak , N. T. , Mauceri , H. J. , Seetharam , S. , Beckett , M. A. , Koons , A. M. , Hari , D. M. , Gupta , V. K. , Reimer , C. , Kalluri , R. , Posner , M. C. , Hellman , S. , Kufe , D. W. and Weichselbaum , R. R. 2000 . NM‐3, an isocoumarin, increases the antitumor effects of radiotherapy without toxicity . Cancer Res. , 60 : 6958 – 6963 .
  • Yin , L. , Ohno , T. , Weichselbaum , R. , Kharbanda , S. and Kufe , D. 2001 . The novel isocoumarin 2‐(8‐hydroxy‐6‐methoxy‐1‐oxo‐1H‐2‐benzopyran‐3‐yl)propionic acid (NM3) induces lethality of human carcinoma cells by generation of reactive oxygen species . Mol. Cancer Ther. , 1 : 43 – 48 .
  • Agata , N. , Nogi , H. , Milhollen , M. , Kharbanda , S. and Kufe , D. 2004 . 2‐(8‐Hydroxy‐6‐methoxy‐1‐oxo‐1H‐2‐benzopyran‐3‐yl)propionic acid, a small molecule isocoumarin, potentiates dexamethasone‐induced apoptosis of human multiple myeloma cells . Cancer Res. , 64 : 8512 – 8516 .
  • Oikawa , T. , Sasaki , M. , Inose , M. , Shimamura , M. , Kuboki , H. , Hirano , S. , Kumagai , H. , Ishizuka , M. and Takeuchi , T. 1997 . Effects of cytogenin, a novel microbial product, on embryonic and tumor cell‐induced angiogenic responses in vivo . Anticancer Res. , 17 : 1881 – 1886 .
  • Nakashima , T. , Hirano , S. , Agata , N. , Kumagai , H. , Isshiki , K. , Yoshioka , T. , Ishizuka , M. , Maeda , K. and Takeuchi , T. 1999 . Inhibition of angiogenesis by a new isocoumarin, NM‐3 . J. Antibiotics , 52 : 426 – 428 .
  • Tsuchida , T. , Kuroda , A. , Nagai , H. , Yoshida , M. , Nakashima , T. , Konuki , K. , Isshiki , K. , Nakamura , H. and Takeuchi , T. 2003 . Convenient total synthesis of NM‐3, an antiangiogenesis agent, and its optical resolution . J. Antibiotics , 56 : 38 – 54 .
  • Yuan , H. , Junker , B. , Helquist , P. and Taylor , R. E. 2004 . Synthesis of anti‐angiogenic isocoumarins . Curr. Org. Synth. , 1 : 1 – 9 .
  • Ichinose , K. , Maeshima , Y. , Yamamoto , Y. , Kinomura , M. , Hirokoshi , K. , Kitayama , H. , Takazawa , Y. , Sugiyama , H. , Yamasaki , Y. , Agata , N. and Makino , H. 2006 . 2‐(8‐Hydroxy‐6‐methoxy‐1‐oxo‐1H‐2‐benzopyran‐3‐yl) propionic acid, an inhibitor of angiogenesis, ameliorates renal alterations in obese type 2 diabetic mice . Diabetes , 55 : 1232 – 1242 .
  • Hallock , Y. F. , Clardy , J. , Kenfield , D. S. and Strobel , G. 1988 . De‐O‐methyldiaporthin, a phytotoxin from Drechslera siccans . Phytochemistry , 27 : 3123 – 3125 .
  • Arnone , A. , Assante , G. , Nasini , G. , Strada , S. and Vercesi , A. 2002 . Cryphonectric acid and other minor metabolites from a hypovirulent strain of Cryphonectria parasitica. . J. Nat. Prod. , 65 : 48 – 50 .
  • Batu , G. and Stevenson , R. 1980 . Synthesis of natural isocoumarins, artemidin and 3‐propylisocoumarin . J. Org. Chem. , 45 : 1532 – 1534 .
  • Sakamoto , T. , Annaka , M. , Kondo , Y. and Yamanaka , H. 1986 . Condensed heteroaromatic ring systems, VIII: Synthesis of 3‐substituted isocoumarins from o‐halobenzoic acid derivatives . Chem. Pharm. Bull. , 34 : 2754 – 2759 .
  • Ogawa , Y. , Maruno , M. and Wakamatsu , T. 1995 . Silver catalyzed cyclization of alkynoic acids: Efficient synthesis of 3‐alkylidenephtalides, γ‐alkylidenebutenolides, and γ‐alkylidenebutyrolactones . Heterocycles , 41 : 2587 – 2599 .
  • Liao , H.‐Y. and Cheng , C.‐H. 1995 . Synthesis of isocoumarins from o‐iodobenzoic acid and terminal acetylenes mediated by palladium complexes and zinc chloride . J. Org. Chem. , 60 : 3711 – 3716 .
  • Sashida , H. and Kawamukai , A. 1999 . Paladium‐catalyzed intramolecular cyclization of o‐ethynylbenzoic acids and o‐ethynylbenzamides: Preparation of isocoumarins and isoquinolin‐1‐ones . Synthesis , : 1145 – 1148 .
  • Bellina , F. , Ciucci , D. , Vergamini , P. and Rossi , R. 2000 . Regioselective synthesis of natural and unnatural (Z)‐3‐(1‐alkylidene)phthalides and 3‐substituted isocoumarins starting from methyl 2‐hydroxybenzoates . Tetrahedron , 56 : 2533 – 2545 .
  • Subramanian , V. , Batchu , V. R. , Barange , D. and Pal , M. 2005 . Synthesis of isocoumarins via Pd/C‐mediated reactions of o‐iodobenzoic acid with terminal alkynes . J. Org. Chem. , 70 : 4778 – 4783 . and references therein
  • Chatterjea , J. N. , Mukherjee , S. K. , Bhakta , C. , Jha , H. C. and Zilliken , F. 1980 . Eine neue Synthese von Tetrahydrocapillarin, o‐Methylglomellin und Oospolacton . Chem. Ber. , 113 : 3927 – 3931 .
  • Elix , J. A. and Jayanthi , V. K. 1987 . The isolation and synthesis of lichen depside 4‐o‐demethylmicrophyllinic acid . Aust. J. Chem. , 40 : 1851 – 1859 .
  • Hauser , F. M. and Baghdanov , V. M. 1988 . A new procedure for regiospecific syntheses of benzopyran‐1‐ones . J. Org. Chem. , 53 : 4676 – 4681 .
  • Mali , R. S. and Babu , K. N. 1998 . Reactions of 3‐(1‐hydroxyalkyl)phthalides with acids: Synthesis of (Z)‐3‐alkylidenephtalides and 3‐alkyl‐8‐hydroxyisocoumarins . J. Org. Chem. , 63 : 2488 – 2492 .
  • Shafiq , Z. , Arfan , M. , Rama , N. H. , Hussain , M. and Hameed , S. 2003 . A Convenient one step synthesis of trans‐artemidin and tetrahydrocapillarin . Indian J. Chem. Sect. B , 42 : 1523 – 1526 .
  • Saeed , A. 2003 . Synthesis and bioactivity of xyridin A and B, metabolites from Xyris indica . J. Heterocycl. Chem. , 40 : 337 – 340 .
  • Piancatelli , G. , D'Auria , M. and D'Onofrio , F. 1994 . Synthesis of 1,4‐dicarbonyl compounds and cyclopentenones from furan . Synthesis , : 867 – 889 . For review, see
  • Butin , A. V. , Krapivin , G. D. , Zavodnik , V. E. and Kul'nevich , V. G. 1993 . Polyfuryl(aryl)alkanes and their derivatives, 7: New recyclization and cyclization reactions in the 2‐hydroxyaryldifurylmethane series . Chem. Heterocycl. Compd. (Engl. Transl.) , 29 : 524 – 533 . Khim. Geterotsikl. Soedin. 1993, 616–626
  • Butin , A. V. , Gutnov , A. V. , Abaev , V. T. and Krapivin , G. D. 1999 . Acid catalyzed reactions of substituted salicylaldehydes with 2‐methylfuran . Molecules , 4 : 52 – 61 .
  • Butin , A. V. , Abaev , V. T. , Mel'chin , V. V. and Dmitriev , A. S. 2005 . Furan ring opening–isochromene ring closure: A new approach to isochromene ring synthesis . Tetrahedron Lett. , 46 : 8439 – 8441 .
  • Butin , A. V. , Smirnov , S. K. and Stroganova , T. A. 2006 . Furan ring opening–indole ring closure: Synthesis of furo[2′,3′:3,4]cyclohepta[1,2‐b]indolium chlorides . J. Heterocycl. Chem. , 43 : 623 – 628 .
  • Abaev , V. T. , Dmitriev , A. S. , Gutnov , A. V. , Podelyakin , S. A. and Butin , A. V. 2006 . Furan ring opening–isocoumarin ring closure: A recyclization reaction of 2‐carboxyaryldifurylmethanes . J. Heterocycl. Chem. , 43 : 1195 – 1204 .
  • Butin , A. V. , Smirnov , S. K. , Stroganova , T. A. , Bender , W. and Krapivin , G. D. 2007 . Simple route to 3‐(2‐indolyl)‐1‐propanones via a furan recyclization reaction . Tetrahedron , 63 : 474 – 491 .
  • Butin , A. V. , Dmitriev , A. S. , Kostyukova , O. N. , Abaev , V. T. and Trushkov , I. V. 2007 . Synthesis of the 4,10‐dihydro‐3H‐pyridazino[1,6‐b]isoquinolin‐10‐one system by a furan recyclization reaction . Synthesis , : 2208 – 2214 .
  • Dmitriev , A. S. , Abaev , V. T. , Bender , W. and Butin , A. V. 2007 . Isoquinolone derivatives via a furan recyclization reaction . Tetrahedron , 63 : 9437 – 9447 .
  • Costa , P. R. R. , Lopes , C. C. , Lopes , R. S. C. , Marinho , M. F. G. and Castro , R. N. 1988 . Vanillin as starting material for the synthesis of isomeric phthalides . Synth. Commun. , 18 : 1723 – 1730 .
  • Starling , S. M. , Raslan , D. S. and de Oliveira , A. B. 1998 . Synthesis of 2‐substituted furanonaphthoquinones using directed metalation and cross coupling reactions . Synth. Commun. , 28 : 1013 – 1030 .
  • Dmitriev , A. S. , Pilipenko , A. S. , Abaev , V. T. and Butin , A. V. 2005 . New synthesis of 3‐(2‐furyl)phthalides . Chem. Heterocycl. Compd. (Engl. Transl.) , 41 : 1102 – 1104 . Khim. Geterotsikl. Soedin. 2005, 1302–1304
  • Zani , C. L. , de Oliveira , A. B. and Snieckus , V. 1987 . Efficient directed ortho metalation‐based route to cytotoxic furanonaphthoquinone natural products . Tetrahedron Lett. , 28 : 6561 – 6564 .
  • Starling , S. M. , Raslan , D. S. , de Oliveira , A. B. and Zani , C. L. 1998 . Synthesis of C‐2 Unsubstituted furanonaphthoquinones . Synth. Commun. , 28 : 3567 – 3578 .
  • Lopes , C. C. , Lima , E. L. S. , Monteiro , A. J. and Costa , P. R. R. 1988 . Synthesis of dimethoxyfuranonaphthoquinones . Synth. Commun. , 18 : 1731 – 1741 .
  • Lopes , C. C. , Lopes , R. S. C. , Pinto , A. V. and Costa , P. R. R. 1984 . Efficient synthesis of cytotoxic quinones: 2‐Acetyl‐4H,9H‐naphtho[2,3‐b]furan‐4,9‐dione (6) and (±)‐2‐(1‐hydroxyethyl)‐4H,9H‐naphtho[2,3‐b]furan‐4,9‐dione (7) . J. Heterocyc. Chem. , 21 : 621 – 622 .
  • Bao‐en , W. 2001 . Ademetionine 1,4‐butanedisulphonate vs. traditional chinese medicine for the treatment of acute viral hepatitis with hepatocellular jaundice . Clin. Drug Invest. , 21 : 685 – 694 .
  • Bao‐en , W. 2001 . Ademetionine 1,4 butanedisulphonate vs traditional chinese medicine for the treatment of hepatocellular jaundice complicating chronic viral hepatitis . Clin. Drug Invest. , 21 : 765 – 773 .
  • Yano , K. 1987 . Minor components from growing buds of Artemisia capillaris that act as insect antifeedants . J. Agric. Food Chem. , 35 : 889 – 891 .

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