Friedel–Crafts Reaction of Activated Benzene Rings with Captodative and Electron‐Deficient Alkenes. A One‐Step Synthesis of the Natural Product Methyl 3‐(2,4,5‐Trimethoxyphenyl)propionate

References

• Knaggs , A. R. 2003 . The biosynthesis of shikimate metabolites . Nat. Prod. Rep. , 20 : 119 – 136 . [PUBMED] [INFOTRIEVE]
   PubMed Web of Science ®Google Scholar
• Nenadis , N. , Zhang , H.‐Y. and Tsimidou , M. Z.J. 2003 . Structure‐antioxidant activity relationship of ferulic acid derivatives: effect of carbon side chain characteristic groups . J. Agric. Food Chem. , 51 : 1874 – 1879 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Petersen , M. and Simmonds , M. S.J. 2003 . Rosmarinic acid . Phytochemistry , 62 : 121 – 125 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Okuda , T. 1999 . Novel aspects of tannins — renewed concepts and structure‐activity relationships . Curr. Org. Chem. , 3 : 609 – 622 .
   Web of Science ®Google Scholar
• Liu , I.‐M. , Chi , T.‐C. , Hsu , F.‐L. , Chen , C.‐F. and Cheng , J.‐T. 1999 . Isoferulic acid as active principle from the rhizoma of Cimicifuga dahurica to lower plasma glucose in diabetic rats . Planta Med. , 65 : 712 – 714 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Zou , Y. , Kim , A. R. , Kim , J. E. , Choi , J. S. and Chung , H. Y. 2002 . Peroxynitrite scavenging activity of sinapic acid (3,5‐dimethoxy‐4‐hydroxycinnamic acid) isolated from Brassica juncea . J. Agric. Food Chem. , 50 : 5884 – 5890 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Yeh , C.‐T. and Yen , G.‐C. 2003 . Effects of phenolic acids on human phenol sulfotransferases in relation to their antioxidant activity . J. Agric. Food Chem. , 51 : 1474 – 1479 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Wende , G. , Waldron , K. W. , Smith , A. C. and Brett , C. T. 1999 . Developmental changes in cell‐wall ferulate and dehydrodiferulates in sugar beet . Phytochemistry , 52 : 819 – 827 . [CROSSREF]
   Web of Science ®Google Scholar
• Exarchou , V. , Nenadis , N. , Tsimidou , M. , Gerothanassis , I. P. , Troganis , A. and Boskou , D. 2002 . Antioxidant activities and phenolic composition of extracts from Greek oregano, Greek sage, and summer savory . J. Agric. Food Chem. , 50 : 5294 – 5299 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Andreasen , M. F. , Landbo , A.‐K. , Christensen , L. P. , Hansen , A. and Meyer , A. S. 2001 . Antioxidant effects of phenolic rye (Secale cereale L.) extracts, monomeric hydroxycinnamates, and ferulic acid dehydrodimers on human low‐density lipoproteins . J. Agric. Food Chem. , 49 : 4090 – 4096 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Grabber , J. H. , Ralph , J. and Hatfield , R. D. 2002 . Model studies of ferulate‐coniferyl alcohol cross‐product formation in primary maize walls: implications for lignification in grasses . J. Agric. Food Chem. , 50 : 6008 – 6016 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Cheng , Z. , Ren , J. , Li , Y. , Chang , W. and Chen , Z. 2002 . Study on the multiple mechanisms underlying the reaction between hydroxyl radical and phenolic compounds by qualitative structure and activity relationship . Bioorg. Med. Chem. , 10 : 4067 – 4073 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Erazo , S. , Negrete , R. , Zaldivar , M. , Backhouse , N. , Delponte , C. , Silva , I. , Belmonte , E. , López‐Pérez , J. L. and San Feliciano , A. 2002 . Methyl psilalate: a new antimicrobial metabolite from Psila boliviensis . Planta Med. , 68 : 66 – 67 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Lee , H.‐S. 2002 . Tyrosinase inhibitors of Pulsatilla cernva root‐derived materials . J. Agric. Food Chem. , 50 : 1400 – 1403 . and references cited therein[PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Etzenhouser , B. , Hansch , C. , Kapur , S. and Selassie , C. D. 2001 . Mechanism of toxicity of esters of caffeic and dihydrocaffeic acids . Bioorg. Med. Chem. , 9 : 199 – 209 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Kawamatsu , Y. , Asakawa , H. , Saraie , T. , Imamiya , E. , Nishikawa , K. and Hamuro , Y. 1980 . Studies on antihyperlipidemic agents. II. Synthesis and biological activities of 2‐chloro‐3‐arylpropionic acids . Arzneim.‐Forsch. , 30 : 585 – 589 .
   PubMed Web of Science ®Google Scholar
• Pieters , L. , Van Dyck , S. , Gao , M. , Bai , R. , Hamel , E. , Vlietinck , A. and Lemiére , G. 1999 . Synthesis and biological evaluation of dihydrobenzofuran lignans and related compounds as potential antitumor agents that inhibit Tubulin polymerization . J. Med. Chem. , 42 : 5475 – 5481 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Kikuzaki , H. , Hisamoto , M. , Hirose , K. , Akiyama , K. and Taniguchi , H. 2002 . Antioxidant properties of ferulic acid and its related compounds . J. Agric. Food Chem. , 50 : 2161 – 2168 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Grabber , J. H. , Ralph , J. and Hatfield , R. D. 2000 . Cross‐linking of maize walls by ferulate dimerization and incorporation into lignin . J. Agric. Food Chem. , 48 : 6106 – 6113 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Ford , J. D. , Huang , K.‐S. , Wang , H.‐B. , Davin , L. B. and Lewis , N. G. 2001 . Biosynthetic pathway to the cancer chemopreventive secoisolariciresinol diglucoside‐hydroxymethyl glutaryl ester‐linked lignan oligomers in flax (Linum usitatissimum) seed . J. Nat. Prod. , 64 : 1388 – 1397 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Bryngelsson , S. , Dimberg , L. H. and Kamal‐Eldin , A. 2002 . Effects of commercial processing on levels of antioxidants in oats (Avena sativa L.) . J. Agric. Food Chem. , 50 : 1890 – 1896 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Lee , E. J. , Kim , S. R. , Kim , J. and Kim , Y. C. 2002 . Hepatoprotective phenylpropanoids from Scrophularia buergeriana roots against CCl4‐induced toxicity: action mechanism and structure‐activity relationship . Planta Med. , 68 : 407 – 411 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Alvarez , L. and Delgado , G. 1999 . C‐ and O‐glycosyl‐α‐hydrodihydrochalcones from Eysenhardtia polistachya . Phytochemistry , 50 : 681 – 687 . [CROSSREF]
   Google Scholar
• Cai , R. , Hettiarachchy , N. S. and Jalaluddin , M. 2003 . High‐performance liquid chromatography determination of phenolic constituents in 17 varieties of cowpeas . J. Agric. Food Chem. , 51 : 1623 – 1627 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Shimoji , Y. , Tamura , Y. , Nakamura , Y. , Nanda , K. , Nishidai , S. , Nishikawa , Y. , Ishihara , N. , Uenakai , K. and Ohigashi , H. 2002 . Isolation and identification of DPPH radical scavenging compounds in kurosu (Japanese unpolished rice vinegar) . J. Agric. Food Chem. , 50 : 6501 – 6503 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Baderschneider , B. and Winterhalter , P. 2001 . Isolation and characterization of novel benzoates, cinnamates, flavonoids, and lignans from Riesling wine and screening for antioxidant activity . J. Agric. Food Chem. , 49 : 2788 – 2798 . [PUBMED] [INFOTRIEVE]
   PubMed Web of Science ®Google Scholar
• Silva , F. A.M. , Borges , F. and Ferreira , M. A. 2001 . Effects of phenolic propyl esters on the oxidative stability of refined sunflower oil . J. Agric. Food Chem. , 49 : 3936 – 3941 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Ioset , J.‐R. , Marston , A. , Gupta , M. P. and Hostettmann , K. 2000 . Antifungal and larvicidal compounds from the root bark of Cordia alliodora . J. Nat. Prod. , 63 : 424 – 426 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Jones , G. 1967 . The Knoevenagel condensation . Org. React. , 15 : 204 – 599 .
   Web of Science ®Google Scholar
• Piccolrovazzi , N. , Pino , P. , Consiglio , G. , Sironi , A. and Moret , M. 1990 . Electronic effects in homogeneous indenylzirconium Ziegler–Natta catalysts . Organometallics , 9 : 3098 – 3105 .
   Web of Science ®Google Scholar
• Delgado , F. , Tamariz , J. , Zepeda , G. , Landa , M. , Miranda , R. and García , J. 1995 . Knoevenagel condensation catalyzed by a Mexican bentonite using infrared irradiation . Synth. Commun. , 25 : 753 – 759 .
   Web of Science ®Google Scholar
• Hatsuda , M. , Kuroda , T. and Seki , M. 2003 . An improved synthesis of (E)‐cinnamic acid derivatives via the Claisen–Schmidt condensation . Synth. Commun. , 33 : 427 – 434 . [CROSSREF]
   Web of Science ®Google Scholar
• Williams , D. B.G. , Lombard , H. and Holzapfel , C. W. 2001 . A comparative study of some Pd‐catalysed Heck reactions in polar‐ and aqueous bi-phasic media . Synth. Commun. , 31 : 2077 – 2081 . [CROSSREF]
   Web of Science ®Google Scholar
• Qandil , A. M. , Miller , D. W. and Nichols , D. E. 1999 . A practical and cost‐effective synthesis of 6,7‐dimethoxy‐2‐tetralone . Synthesis , : 2033 – 2035 . [CROSSREF]
   Web of Science ®Google Scholar
• Vallin , K. S.A. , Emilsson , P. , Larhed , M. and Hallberg , A. 2002 . High‐speed Heck reactions in ionic liquid with controlled microwave heating . J. Org. Chem. , 67 : 6243 – 6246 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Heck , R. F. 1982 . Palladium‐catalyzed vinylation of organic halides . Org. React. , 27 : 345 – 390 .
   Web of Science ®Google Scholar
• Permutter , P. 1992 . Conjugate Addition Reactions in Organic Synthesis 199 – 282 . Oxford : Pergamon Press .
   Google Scholar
• Malmberg , H. , Nilsson , M. and Ullenius , C. 1982 . Stereoselectivity in the transfer of the 2‐(1‐dimethylaminoethyl)phenyl group, R*, from LiR2*Cu and LiR*(2‐thienyl)Cu to enones . Tetrahedron Lett. , 23 : 3823 – 3826 . [CROSSREF]
   Web of Science ®Google Scholar
• Lipshutz , B. H. and Sengupta , S. 1992 . Organocopper reagents: substitution, conjugate addition, carbo/metallocupration, and other reactions . Org. React. , 41 : 135 – 631 .
   Google Scholar
• Olah , G. A. , Krishnamurti , R. and Prakash , G. K.S. 1991 . “ Friedel–Crafts alkylations ” . In Comprehensive Organic Synthesis Edited by: Trost , B. M. and Fleming , I. Vol. 3 , 293 – 339 . Oxford : Pergamon Press .
   Google Scholar
• Mahindaratne , M. P.D. and Wimalasena , K. 1998 . Detailed characterization of p‐toluenesulfonic acid monohydrate as a convenient, recoverable, safe, and selective catalyst for alkylation of the aromatic nucleus . J. Org. Chem. , 63 : 2858 – 2866 . [CROSSREF]
   Web of Science ®Google Scholar
• Shen , Y.‐s. S. , Liu , H.‐x. and Chen , Y.‐q . 1990 . The first Friedel‐Crafts reaction of nitrobenzene . J. Org. Chem. , 55 : 3961 – 3962 .
   Web of Science ®Google Scholar
• Bunce , R. A. and Reeves , H. D. 1989 . Amberlyst‐15 catalyzed addition of phenols to α,β‐unsaturated ketones . Synth. Commun. , 19 : 1109 – 1117 .
   Web of Science ®Google Scholar
• Yadav , J. S. , Abraham , S. , Reddy , B. V.S. and Sabitha , G. 2001 . InCl3‐catalysed conjugate addition of indoles with electron‐deficient olefins . Synthesis , : 2165 – 2169 . [CROSSREF]
   Web of Science ®Google Scholar
• Jensen , K. B. , Thorhauge , J. , Hazell , R. G. and Jørgensen , K. A. 2001 . Catalytic asymmetric Friedel‐Crafts alkylation of β,γ‐unsaturated α‐ketoesters: enantioselective addition of aromatic C–H bonds to alkenes . Angew. Chem., Int. Ed. , 40 : 160 – 163 . [CROSSREF]
   Google Scholar
• Tateiwa , J.‐l. , Horiuchi , H. , Hashimoto , K. , Yamauchi , T. and Uemura , S. 1994 . Cation‐exchanged montmorillonite‐catalyzed facile Friedel‐Crafts alkylation of hydroxy and methoxy aromatics with 4‐hydroxybutan‐2‐ones to produce rasberry ketone and some pharmaceutically active compounds . J. Org. Chem. , 59 : 5901 – 5904 .
   Web of Science ®Google Scholar
• Reyes , A. , Aguilar , R. , Muñoz , A. H. , Zwick , J.‐C. , Rubio , M. , Escobar , J.‐L. , Soriano , M. , Toscano , R. and Tamariz , J. 1990 . Highly selective Diels‐Alder cycloadditions of captodative dienophiles 1‐acetylvinyl arenecarboxylates to unsymmetrically substituted butadienes . J. Org. Chem. , 55 : 1024 – 1034 .
   Web of Science ®Google Scholar
• Peralta , J. , Bullock , J. P. , Bates , R. W. , Bott , S. , Zepeda , G. and Tamariz , J. 1995 . Stereoselective synthesis, NMR conformational study and Diels‐Alder reaction of β‐functionalized 1‐acetylvinyl arenecarboxylates . Tetrahedron , 51 : 3979 – 3996 . [CROSSREF]
   Web of Science ®Google Scholar
• Ochoa , M. E. , Arias , A. S. , Aguilar , R. , Delgado , F. and Tamariz , J. 1999 . Captodative olefin 3‐p‐nitrobenzoyloxy‐3‐buten‐2‐one as a Diels‐Alder ketene equivalent for the synthesis of γ‐hydroxycyclohexenones . Tetrahedron , 55 : 14535 – 14546 . [CROSSREF]
   Web of Science ®Google Scholar
• Herrera , R. , Nagarajan , A. , Morales , M. A. , Méndez , F. , Jiménez‐Vázquez , H. A. , Zepeda , G. and Tamariz , J. 2001 . Regio‐ and stereoselectivity of captodative olefins in 1,3‐dipolar cycloadditions. A DFT/HSAB theory rationale for the observed regiochemistry of nitrones . J. Org. Chem. , 66 : 1252 – 1263 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Díaz , F. , Muñoz , H. , Labarrios , F. , Chamorro , G. , Salazar , M. , Morelos , M. E. and Tamariz , J. 1993 . Synthesis and hypolipidemic activity of some α‐asarone analogs . Med. Chem. Res. , 3 : 101 – 109 .
   Google Scholar
• Labarrios , F. , Garduño , L. , Vidal , M. R. , García , R. , Salazar , M. , Martínez , E. , Díaz , F. , Chamorro , G. and Tamariz , J. 1999 . Synthesis and hypolipidaemic evaluation of a series of α‐asarone analogues related to clofibrate in mice . J. Pharm. Pharmacol. , 51 : 1 – 7 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Cruz , A. , Garduño , L. , Salazar , M. , Martínez , E. , Jiménez‐Vázquez , H. A. , Díaz , F. , Chamorro , G. and Tamariz , J. 2001 . Synthesis and hypolipidemic activity of modified side chain α‐asarone homologues . Arzneim.‐Forsch. , 51 : 535 – 544 .
   PubMed Web of Science ®Google Scholar
• Johnston , H. W. and Gross , F. J. 1957 . Cyanoethylation of phenol; isolation of an ortho‐addition product . J. Org. Chem. , 22 : 1264 – 1265 .
   Web of Science ®Google Scholar
• Chatterjee , A. and Hazra , B. G. 1977 . Carbon–carbon cyanoethylation of anisole and its derivatives . Tetrahedron , 33 : 1983 – 1987 . [CROSSREF]
   Web of Science ®Google Scholar
• Hazra , B. G. , Pore , V. S. and Basu , S. 1995 . Titanium tetrachloride‐mediated carbon–carbon chlorocyanoethylation of anisole: synthesis of tyrosine derivatives . Synthetic Commun. , 25 : 2847 – 2855 .
   Web of Science ®Google Scholar
• Westfahl , L. and Gresham , T. L. 1954 . Vinylidene cyanide. V. The aluminum chloride catalyzed reaction of vinylidene cyanide and aromatic compounds . J. Am. Chem. Soc. , 76 : 1076 – 1080 .
   Web of Science ®Google Scholar
• Martínez , R. , Jiménez‐Vázquez , H. A. and Tamariz , J. 2000 . Regioselective synthesis of N‐substituted 4‐methylene‐2‐oxazolidinones and 4‐oxazolin‐2‐ones. Study of reactivity in thermal Michael conjugate additions . Tetrahedron , 56 : 3857 – 3866 . [CROSSREF]
   Web of Science ®Google Scholar
• Narayana , M. , Dash , J. F. and Gardner , P. D. 1962 . Phosphorus acids in organic systems. III. Specific pyrophosphoric acid catalysis in the conversion of resorcinol dimethyl ether to coumarins . J. Org. Chem. , 27 : 4704 – 4705 .
   Web of Science ®Google Scholar
• Chamorro , G. , Salazar , M. , Salazar , S. and Mendoza , T. 1993 . Farmacología y toxicología de Guatteria gaumeri y α‐asarona . Rev. Inv. Clin. , 45 : 597 – 604 . and references cited therein
   PubMedGoogle Scholar
• Göggelmann , W. and Schimmer , O. 1983 . Mutagenicity testing of β‐asarone and commercial calamus drugs with Salmonella typhimurium . Mutation Res. , 121 : 191 – 194 . [CROSSREF]
   PubMedGoogle Scholar
• Abel , G. 1987 . Chromosomenschädigende wirkung von β‐asaron in menschlichen lymphocyten . Planta Med. , 53 : 251 – 253 . [PUBMED] [INFOTRIEVE]
   PubMedGoogle Scholar
• Sinha , A. K. , Dogra , R. and Joshi , B. P. 2002 . A concise conversion of β‐asarone to 1‐(2‐carbomethoxyethyl)‐2,4,5‐trimethoxybenzene occurring in Cordia alliodora . Ind. J. Chem. , 41B : 635 – 638 . Section B
   Google Scholar
• Vanisree , M. , Kavitha , J. and Subbaraju , G. V. 2002 . Synthesis of methyl 3‐(2,4,5‐trimethoxyphenyl)propionate, an antifungal and larvicidal constituent of Cordia alliodora . Asian J. Chem. , 14 : 534 – 536 .
   Google Scholar
• Fleming , I. 1976 . Frontier Orbitals and Organic Chemical Reactions Chichester : John Wiley & Sons .
   Google Scholar
• Jiménez‐Vázquez , H. A. , Ochoa , M. E. , Zepeda , G. , Modelli , A. , Jones , D. , Mendoza , J. A. and Tamariz , J. 1997 . Structural, spectroscopic, and theoretical study of 1‐acetylvinyl p‐nitrobenzoate, a highly reactive and selective captodative olefin in cycloaddition reactions . J. Phys. Chem. A , 101 : 10082 – 10089 . [CROSSREF]
   Web of Science ®Google Scholar
• Herrera , R. , Jiménez‐Vázquez , H. A. , Modelli , A. , Jones , D. , Söderberg , B. C. and Tamariz , J. 2001 . Synthesis of new captodative alkenes: alkyl 2‐aroyloxy acrylates — structure, and reactivity in Diels‐Alder cycloadditions . Eur. J. Org. Chem. , : 4657 – 4669 . [CROSSREF]
   Web of Science ®Google Scholar
• Aldous , F. A.B. , Barrass , B. C. , Brewster , K. , Buxton , D. A. , Green , D. M. , Pinder , R. M. , Rich , P. , Skeels , M. and Tutt , K. J. 1974 . Structure‐activity relationships in psychotomimetic phenylalkylamines . J. Med. Chem. , 17 : 1100 – 1111 . [PUBMED] [INFOTRIEVE]
   PubMed Web of Science ®Google Scholar
• De Lombaert , S. , Blanchard , L. , Stamford , L. B. , Tan , J. , Wallace , E. M. , Satoh , Y. , Fitt , J. , Hoyer , D. , Simonsbergen , D. , Moliterni , J. , Marcopoulos , N. , Savage , P. , Chou , M. , Trapani , A. J. and Jeng , A. Y. 2000 . Potent and selective non‐peptidic inhibitors of endothelin‐converting enzyme‐1 with sustained duration of action . J. Med. Chem. , 43 : 488 – 504 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar