Concise and Efficient Synthesis of Linear Furocoumarins: Psoralen and 4‐Methylpsoralen

References

• Bethea , D. , Fullmer , B. , Syed , S. , Seltzer , G. , Tiano , J. , Rischko , C. , Gillespie , L. , Brown , D. and Gasparro , F. P. 1999 . Psoralen photobiology and photochemotherapy: 50 years of science and medicine . J. Dermatol. Sci. , 19 : 78 – 88 .
   PubMed Web of Science ®Google Scholar
• Grundmann , K. M. , Ludwig , R. , Zollner , T. M. , Ochsendorf , F. , Thaci , D. , Boehncke , W. H. , Krutmann , J. , Kaufmann , R. and Podda , M. 2004 . Narrowband UVB and cream psoralen–UVA combination therapy for plaque‐type psoriasis . J. Am. Acad. Dermatol. , 50 : 734 – 739 .
   Google Scholar
• Park , J. H. and Lee , M. H. 2004 . Case of leukoderma punctata after topical PUVA treatment . Int. J. Dermatol. , 43 : 138 – 139 .
   Google Scholar
• Petering , H. , Breuer , C. , Herbst , R. , Kapp , A. and Werfel , T. 2004 . Comparison of localized high‐dose UVA1 irradiation versus topical cream psoralen‐UVA for treatment of chronic vesicular dyshidrotic eczema . J. Am. Acad. Dermatol. , 50 : 68 – 72 .
   PubMed Web of Science ®Google Scholar
• Diederen , P. V. M. M. , Weelden , H. , Sanders , C. J. G. , Toonstra , J. and Vloten , W. A. 2003 . Narrowband UVB and psoralen‐UVA in the treatment of early‐stage mycosis fungoides: A retrospective study . J. Am. Acad. Dermatol. , 48 : 215 – 219 .
   PubMed Web of Science ®Google Scholar
• Miolo , G. , Tomanin , R. , Rossi , A. D. , Dall'Acqua , F. , Zacchello , F. and Scarpa , M. 1994 . Antiretroviral activity of furocoumarins plus UVA light detected by a replication‐defective retrovirus . J. Photochem. Photobiol. B. , 26 : 241 – 247 .
   Google Scholar
• Lage , C. , Pádula , M. , Alencar , T. A. M. , Gonçalves , S. R. F. , Vidal , L. S. , Cabral‐Neto , J. and Leitão , A. C. 2003 . New insights on how nucleotide excision repair could remove DNA adducts induced by chemotherapeutic agents and psoralens plus UV‐A (PUVA) in Escherichia coli cells . Mutat. Res. Rev. Mutat. , 544 : 143 – 157 .
   PubMedGoogle Scholar
• Islas , A. L. , Vos , J. M. and Hanawalt , P. C. 1991 . Differential introduction and repair of psoralen photoadducts to DNA in specific human genes . Cancer Res. , 51 : 2867 – 2873 .
   PubMedGoogle Scholar
• Edelson , R. L. , Russell‐Jones , R. , Whittaker , S. and Fraser‐Andrews , E. 1999 . Sezary syndrome, cutaneous T‐cell lymphoma, and extracorporeal photopheresis . Arch. Dermatol. , 135 : 600 – 601 .
   PubMedGoogle Scholar
• Goupil , J. J. Utilisation du 5‐methoxypsoralene dans le traitement du sida . French Patent 2,698, 270 . 1994 .
   Google Scholar
• Goaster , J. L. Utilisation de derives benzofuranniques ou benzopyranniques dans la prevention et le traitement des infections a retrovirus . French Patent 2,691,629 . 1993 .
   Google Scholar
• Legitimo , A. , Consolini , R. , DiStefano , R. , Bencivelli , W. and Mosca , F. 2002 . Psoralen and UVA light: An in vitro investigation of multiple immunological mechanisms underlying the immunosuppression induction in allograft rejection . Blood Cells Mol. Dis. , 29 : 24 – 34 .
   Google Scholar
• Bordin , F. , Carlassare , F. , Busulini , L. and Baccichetti , F. 1993 . Furanocoumarin sensitization induces DNA–protein cross‐links . Photochem. Photobiol. , 58 : 133 – 136 .
   Google Scholar
• Di Noto , V. , Via , L. D. , Gia , O. , Onori , A. M. , Cellai , L. and Magno , S. M. 2000 . J. Phys. Chem. B. , 104 : 4992 – 4999 .
   Google Scholar
• Spath , E. and Pailer , M. 1934 . Synthese des angelicins . Ber. , 67 : 1212 – 1213 .
   Google Scholar
• Kaufman , K. D. , Erb , D. J. , Blok , T. M. , Carlson , R. W. , Knoechel , D. J. , McBride , L. and Zeitlow , T. 1982 . Reactions of furocoumarins, II(1): Synthetic aminomethyl psoralens via chloromethylation or benzylic bromination . J. Heterocycl. Chem. , 19 : 1051 – 1056 .
   Google Scholar
• Nore , P. and Honkanen , E. 1980 . A new synthesis of methoxalen . J. Heterocycl. Chem. , 17 : 985 – 987 .
   Google Scholar
• MacLeod , J. K. and Worth , B. R. 1972 . Synthesis of benzofuranoid systems I: Furocoumarins, benzofurans and dibenzofurans . Tetrahedron Lett. , 13 : 237 – 240 .
   Google Scholar
• Esse , R. C. and Christensen , B. E. 1960 . Psoralenes, III: Cyclization studies of certain substituted coumarins and coumarans . J. Org. Chem. , 25 : 1565 – 1569 .
   Google Scholar
• Zhang , B. L. , Wang , F. D. and Yue , J. M. 2006 . A new efficient method for the total synthesis of linear furocoumarins . Synlett , : 567 – 570 .
   Google Scholar
• Ahluwalia , V. K. , Prakash , C. and Bala , S. 1980 . A convenient synthesis of psoralen derivatives: Psoralen, 4‐methyl‐psoralen and 4‐phenyl‐psoralen . Monatsh. Chem. , 111 : 877 – 882 .
   Google Scholar
• Zubia , E. , Luis , F. R. , Massanet , G. M. and Collado , I. G. 1992 . An efficient synthesis of furanocoumarins . Tetrahedron , 48 : 4239 – 4246 .
   Google Scholar
• Aquila , B. M. 1997 . A new synthesis of 8‐methylpsoralen utilizing a palladium‐copper catalyzed reaction to generate the furan ring and thus allowing for the generation of novel analogs in the 5′‐position . Tetrahedron Lett. , 38 : 2795 – 2798 .
   Google Scholar
• Chimichi , S. , Boccalini , M. , Cosimelli , B. , Viola , G. , Vedaldi , D. and Dall'Acqua , F. 2002 . A convenient synthesis of psoralens . Tetrahedron , 58 : 4859 – 4863 .
   Google Scholar
• Chimichi , S. , Boccalini , M. and Cosimelli , B. 2002 . A new convenient route to 2‐oxoethoxycoumarins: key intermediates in the synthesis of natural products . Tetrahedron , 58 : 4851 – 4858 .
   Web of Science ®Google Scholar
• Hayakawa , K. , Yodo , M. , Ohsuki , S. and Kanematsu , K. 1984 . Novel bicycloannulation via tandem vinylation and intramolecular Diels–Alder reaction of five‐membered heterocycles: A new approach to construction of psoralen and azapsoralen . J. Am. Chem. Soc. , 106 : 6735 – 6740 .
   Web of Science ®Google Scholar
• Mal , D. , Bandhyopadhyay , M. , Datta , K. and Murty , K. V. S. N. 1998 . Anionic [4+2] cycloaddition strategy to linear furocoumarins: Synthesis of 8‐methoxypsoralen and its isoster . Tetrahedron , 54 : 7525 – 7538 .
   Google Scholar
• Mal , D. , Murty , K. V. S. N. and Datta , K. 1994 . A sequential anionic [4+2] cycloaddition and thermal [4+2] cycloreversion strategy to furocoumarins: A concise synthesis of methoxsalen . Tetrahedron Lett. , 35 : 9617 – 9618 .
   Google Scholar
• Piancatelli , G. , Scettri , A. and Dauria , M. 1982 . Pyridinium chlorochromate: A versatile oxidant in organic synthesis . Synthesis , 4 : 245 – 258 .
   Web of Science ®Google Scholar
• Fatiadi , A. J. 1987 . The classical permanganate ion: Still a novel oxidant in organic chemistry . Synthesis , 2 : 85 – 125 .
   Google Scholar
• Tidwell , T. T. 1990 . Oxidation of alcohols by activated dimethyl sulfoxide and related reactions: An update . Synthesis , 10 : 857 – 870 .
   Google Scholar
• Singh , P. R. , Singh , D. U. and Samant , S. D. 2004 . Sulphamic acid—an efficient and cost‐effective solid acid catalyst for the Pechmann reaction . Synlett , 11 : 1909 – 1912 .
   Google Scholar
• Crisp , G. T. and Millan , M. J. 1998 . Conjugate addition of amino acid side chains to dyes containing alkynone, alkynoic ester and alkynoic amide linker arms . Tetrahedron , 54 : 649 – 666 .
   Google Scholar
• Chatterjee , D. K. , Chatterje , R. M. and Sen , K. 1964 . Studies on the ultraviolet absorption of psoralene and substituted psoralenes . J. Org. Chem. , 29 : 2467 – 2469 .
   Google Scholar