메뉴 건너뛰기




Volumn 80, Issue 9, 2007, Pages 1672-1690

Total synthesis of epoxyquinonoid natural products

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLOYL CHLORIDES; ASYMMETRIC TOTAL SYNTHESIS; CARBOXYPALLADATION; CASCADE REACTIONS; DIELS-ALDER REACTIONS; DIENOPHILE; DIENOPHILES; ELECTROCYCLIZATION; GENERATION SYNTHESIS; KEY INTERMEDIATES; KEY REACTIONS; KINETIC RESOLUTIONS; NATURAL PRODUCTS; ONE STEPS; POLYCYCLIC COMPOUNDS; TOTAL SYNTHESES;

EID: 58149301633     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.80.1672     Document Type: Article
Times cited : (14)

References (160)
  • 2
    • 0030952289 scopus 로고    scopus 로고
    • b) W. Risau, Nature 1997, 386, 671.
    • (1997) Nature , vol.386 , pp. 671
    • Risau, W.1
  • 18
    • 4344612772 scopus 로고    scopus 로고
    • Review of naturally occurring cyclohexane epoxides, see
    • Review of naturally occurring cyclohexane epoxides, see: J. Marco-Contelles, M. T. Molina, S. Anjum, Chem. Rev. 2004, 104, 2857.
    • (2004) Chem. Rev , vol.104 , pp. 2857
    • Marco-Contelles, J.1    Molina, M.T.2    Anjum, S.3
  • 20
    • 30744456247 scopus 로고    scopus 로고
    • Review of biomimetic electrocyclizations, see
    • Review of biomimetic electrocyclizations, see: C. M. Beaudry, J. P. Malerich, D. Trauner, Chem. Rev. 2005, 105, 4757;
    • (2005) Chem. Rev , vol.105 , pp. 4757
    • Beaudry, C.M.1    Malerich, J.P.2    Trauner, D.3
  • 44
    • 58149300519 scopus 로고
    • Jpn. Kokai Tokkyo Koho 03041075, Chem. Ahstr. 1991, 115, 181517
    • K. Kawazu, A. Kobayashi, K. Oe, Jpn. Kokai Tokkyo Koho 03041075, 1991, Chem. Ahstr. 1991, 115, 181517.
    • (1991)
    • Kawazu, K.1    Kobayashi, A.2    Oe, K.3
  • 62
    • 58149288918 scopus 로고    scopus 로고
    • Recent review of asymmetric Diels-Alder reactions: Y. Hayashi, in Catalytic Asymmetric Diels-Alder Reactions in Cyclo-addition Reactions in Organic Synthesis, ed. by S. Kobayashi, K. A. Jørgensen, Wiley-VCH, Weinheim, 2001, pp. 5-56;
    • Recent review of asymmetric Diels-Alder reactions: Y. Hayashi, in Catalytic Asymmetric Diels-Alder Reactions in Cyclo-addition Reactions in Organic Synthesis, ed. by S. Kobayashi, K. A. Jørgensen, Wiley-VCH, Weinheim, 2001, pp. 5-56;
  • 63
    • 0030845835 scopus 로고    scopus 로고
    • Review of Diels-Alder reaction of furan: C. O. Kappe, S. S. Murphree, A. Padwa, Tetrahedron 1997, 53, 14179;
    • Review of Diels-Alder reaction of furan: C. O. Kappe, S. S. Murphree, A. Padwa, Tetrahedron 1997, 53, 14179;
  • 64
    • 85004105927 scopus 로고    scopus 로고
    • Review of optically pure 7-oxabicyclo[2.2.1]hept-5-en-2-yl derivatives: P. Vogel, D. Fattori, F. Gasparini, C. Le Drian, Synlett 1990, 173.
    • Review of optically pure 7-oxabicyclo[2.2.1]hept-5-en-2-yl derivatives: P. Vogel, D. Fattori, F. Gasparini, C. Le Drian, Synlett 1990, 173.
  • 65
    • 0000667771 scopus 로고    scopus 로고
    • Maleic anhydride or maleimide: a W. Shih, N. Lau, S. Seltzer, J. Org. Chem. 1975, 40, 1269.
    • Maleic anhydride or maleimide: a) W. Shih, N. Lau, S. Seltzer, J. Org. Chem. 1975, 40, 1269.
  • 71
    • 0011749630 scopus 로고
    • Dimethyl acetylenedicarboxylate
    • g) M. Tada, N. Mutoh, T. Shimizu, J. Org. Chem. 1995, 60, 550. Dimethyl acetylenedicarboxylate:
    • (1995) J. Org. Chem , vol.60 , pp. 550
    • Tada, M.1    Mutoh, N.2    Shimizu, T.3
  • 74
    • 0028111622 scopus 로고    scopus 로고
    • J. Gustafsson, O. Sterner, J. Org. Chem. 1994, 59, 3994. Acrylic acid:
    • j) J. Gustafsson, O. Sterner, J. Org. Chem. 1994, 59, 3994. Acrylic acid:
  • 78
    • 0029919983 scopus 로고    scopus 로고
    • W. G. Dauben, J. Y. L. Lam, Z. R. Guo, J. Org. Chem. 1996, 61, 4816.
    • b) W. G. Dauben, J. Y. L. Lam, Z. R. Guo, J. Org. Chem. 1996, 61, 4816.
  • 84
    • 0021522012 scopus 로고    scopus 로고
    • 2: H. Kotsuki, K. Asao, H. Ohnishi, Bull. Chem. Soc. Jpn. 1984, 57, 3339.
    • 2: H. Kotsuki, K. Asao, H. Ohnishi, Bull. Chem. Soc. Jpn. 1984, 57, 3339.
  • 85
    • 0000789661 scopus 로고    scopus 로고
    • 6: W. A. Nugent, R. J. McKinney, R. L. Harlow, Organometallics 1984, 3, 1315.
    • 6: W. A. Nugent, R. J. McKinney, R. L. Harlow, Organometallics 1984, 3, 1315.
  • 86
    • 0000690423 scopus 로고    scopus 로고
    • III-doped K10 clay: P. Laszlo, J. Lucchetti, Tetrahedron Lett. 1984, 25, 4387.
    • III-doped K10 clay: P. Laszlo, J. Lucchetti, Tetrahedron Lett. 1984, 25, 4387.
  • 88
    • 8744246800 scopus 로고    scopus 로고
    • 2: V. V. Veselovsky, A. S. Gybin, A. V. Lozanova, A. M. Moissenkov, W. A. Smit, R. Caple, Tetrahedron Lett. 1988, 29, 175.
    • 2: V. V. Veselovsky, A. S. Gybin, A. V. Lozanova, A. M. Moissenkov, W. A. Smit, R. Caple, Tetrahedron Lett. 1988, 29, 175.
  • 90
    • 37049071711 scopus 로고    scopus 로고
    • III-doped clay: J. M. Adamas, S. Dyer, K. Martin, W. A. Matear, R. W. McCabe, J. Chem. Soc., Perkin Trans. 1 1994, 761.
    • III-doped clay: J. M. Adamas, S. Dyer, K. Martin, W. A. Matear, R. W. McCabe, J. Chem. Soc., Perkin Trans. 1 1994, 761.
  • 91
    • 0030872663 scopus 로고    scopus 로고
    • 2: J. M. Fraile, J. I. Garcia, J. Massam, J. A. Mayoral, E. Pires, J. Mol. Catal. A: Chem. 1997, 123, 43.
    • 2: J. M. Fraile, J. I. Garcia, J. Massam, J. A. Mayoral, E. Pires, J. Mol. Catal. A: Chem. 1997, 123, 43.
  • 92
    • 58149290512 scopus 로고    scopus 로고
    • 3: B. Garrigues, A. Oussaid, J. Organomet. Chem. 1999, 585, 253.
    • 3: B. Garrigues, A. Oussaid, J. Organomet. Chem. 1999, 585, 253.
  • 93
    • 58149290513 scopus 로고    scopus 로고
    • 2 10%.
    • 2 10%.
  • 94
    • 0034634399 scopus 로고    scopus 로고
    • 4 have been employed as unique Lewis acid catalysts in the following reactions: a) Direct condensation reaction of carboxylic acids with alcohols: K. Ishihara, S. Ohara, H. Yamamoto, Science 2000, 290, 1140.
    • 4 have been employed as unique Lewis acid catalysts in the following reactions: a) Direct condensation reaction of carboxylic acids with alcohols: K. Ishihara, S. Ohara, H. Yamamoto, Science 2000, 290, 1140.
  • 95
    • 58149296839 scopus 로고    scopus 로고
    • Friedel-Crafts acylation: I. Hachiya, M. Morikawa, S. Kobayashi, Bull. Chem. Soc Jpn. 1995, 68, 2053.
    • b) Friedel-Crafts acylation: I. Hachiya, M. Morikawa, S. Kobayashi, Bull. Chem. Soc Jpn. 1995, 68, 2053.
  • 96
    • 0000568181 scopus 로고    scopus 로고
    • Fries rearrangement: S. Kobayashi, M. Morikawa, I. Hachiya, Bull. Chem. Soc. Jpn. 1997, 70, 267.
    • c) Fries rearrangement: S. Kobayashi, M. Morikawa, I. Hachiya, Bull. Chem. Soc. Jpn. 1997, 70, 267.
  • 97
    • 0035823816 scopus 로고    scopus 로고
    • Intramolecular aryl silylation: N. Asao, T. Shimada, T. Shimada, Y. Yamamoto, J. Am. Chem. Soc. 2001, 123, 10899.
    • d) Intramolecular aryl silylation: N. Asao, T. Shimada, T. Shimada, Y. Yamamoto, J. Am. Chem. Soc. 2001, 123, 10899.
  • 98
    • 0034966427 scopus 로고    scopus 로고
    • Asymmetric Michael addition of thiols: S. Kobayashi, C. Ogawa, M. Kawamura, M. Sugiura, Synlett 2001, 983.
    • e) Asymmetric Michael addition of thiols: S. Kobayashi, C. Ogawa, M. Kawamura, M. Sugiura, Synlett 2001, 983.
  • 99
    • 0035823771 scopus 로고    scopus 로고
    • 1,3-Cycloaddition of N-tert-butylarylmethylideneamine N-oxides: P. J. Dunn, A. B. Graham, R. Grigg, P. Higginson, V. Sridharan, M. Thornton-Pett, Chem. Commun. 2001, 1968.
    • f) 1,3-Cycloaddition of N-tert-butylarylmethylideneamine N-oxides: P. J. Dunn, A. B. Graham, R. Grigg, P. Higginson, V. Sridharan, M. Thornton-Pett, Chem. Commun. 2001, 1968.
  • 100
    • 58149300409 scopus 로고    scopus 로고
    • 2O: 71%, endo/exo = 92/8.
    • 2O: 71%, endo/exo = 92/8.
  • 101
    • 58149284374 scopus 로고    scopus 로고
    • Catalytic asymmetric reaction by the use of a chiral Lewis acid
    • Catalytic asymmetric reaction by the use of a chiral Lewis acid:
  • 104
    • 0031013777 scopus 로고    scopus 로고
    • Diastereo-selective reaction by the use of chiral dienophile
    • c) D. A. Evans, D. M. Barnes, Tetrahedron Lett. 1997, 38, 57. Diastereo-selective reaction by the use of chiral dienophile:
    • (1997) Tetrahedron Lett , vol.38 , pp. 57
    • Evans, D.A.1    Barnes, D.M.2
  • 114
    • 5444248415 scopus 로고    scopus 로고
    • 3).
    • 3).
  • 118
    • 58149280020 scopus 로고    scopus 로고
    • In our previous paper,9a the Dess-Martin periodinane was employed as the oxidant, which gave the desired product in good yield. TEMPO oxidation is suitable for large-scale preparation. P. L. Anelli, F. Montanari, S. Quici, Org. Synth. 1993, Coll. VIII, 367
    • 9a the Dess-Martin periodinane was employed as the oxidant, which gave the desired product in good yield. TEMPO oxidation is suitable for large-scale preparation. P. L. Anelli, F. Montanari, S. Quici, Org. Synth. 1993, Coll. Vol. VIII, 367.
  • 129
    • 0021522012 scopus 로고    scopus 로고
    • The Diels-Alder reaction of methyl acrylate and furan: a H. Kotsuki, K. Asao, H. Ohnishi, Bull. Chem. Soc Jpn. 1984, 57, 3339.
    • The Diels-Alder reaction of methyl acrylate and furan: a) H. Kotsuki, K. Asao, H. Ohnishi, Bull. Chem. Soc Jpn. 1984, 57, 3339.
  • 133
    • 58149278021 scopus 로고
    • The Diels-Alder reaction under high pressure
    • e) D. J. Ager, M. B. East, Heterocycles 1994, 37, 1789. The Diels-Alder reaction under high pressure:
    • (1789) Heterocycles , vol.37
    • Ager, D.J.1    East, M.B.2
  • 135
    • 33847797751 scopus 로고
    • The Diels-Alder reaction of acrylic acid and furan
    • g) W. G. Dauben, H. O. Krabbenhoft, J. Am. Chem. Soc 1976, 98, 1992. The Diels-Alder reaction of acrylic acid and furan:
    • (1976) J. Am. Chem. Soc , vol.98
    • Dauben, W.G.1    Krabbenhoft, H.O.2
  • 137
    • 37049098045 scopus 로고
    • Holmes, Jennings-White, et al. have elegantly synthesized cis-maneonene A using a similar sequence involving the Diels-Alder reaction of furan and fumaroyl chloride, followed by hydrolysis and bromolactonization, see
    • Holmes, Jennings-White, et al. have elegantly synthesized cis-maneonene A using a similar sequence involving the Diels-Alder reaction of furan and fumaroyl chloride, followed by hydrolysis and bromolactonization, see: C. L. D. Jennings-White, A. B. Holmes, P. R. Raithby, J. Chem. Soc., Chem. Commun. 1979, 542.
    • (1979) J. Chem. Soc., Chem. Commun , pp. 542
    • Jennings-White, C.L.D.1    Holmes, A.B.2    Raithby, P.R.3
  • 140
    • 58149290423 scopus 로고    scopus 로고
    • All calculations were performed with the program package TITAN 1.0.5 of Schrödinger, Inc. (http://www.schrodinger.com) and Wavefunction Inc. (http://www.wavefun.com).
    • All calculations were performed with the program package TITAN 1.0.5 of Schrödinger, Inc. (http://www.schrodinger.com) and Wavefunction Inc. (http://www.wavefun.com).
  • 141
    • 0035851398 scopus 로고    scopus 로고
    • See footnote 18 of Ref. 14a. a J. C. C. Atherton, S. Jones, Tetrahedron Lett. 2001, 42, 8239.
    • See footnote 18 of Ref. 14a. a) J. C. C. Atherton, S. Jones, Tetrahedron Lett. 2001, 42, 8239.
  • 144
    • 0041810236 scopus 로고    scopus 로고
    • For excellent reviews of biosynthetic Diels-Alder reactions, see
    • d) For excellent reviews of biosynthetic Diels-Alder reactions, see: E. M. Stocking, R. M. Williams, Angew. Chem., Int. Ed. 2003, 42, 3078.
    • (2003) Angew. Chem., Int. Ed , vol.42 , pp. 3078
    • Stocking, E.M.1    Williams, R.M.2
  • 156
    • 58149280021 scopus 로고    scopus 로고
    • The reason of the effect of the concentration on the dia- stereoselectivity is not clear
    • The reason of the effect of the concentration on the dia- stereoselectivity is not clear.
  • 160
    • 0141656406 scopus 로고    scopus 로고
    • The preliminary results have been published. H. Kakeya, Y. Miyake, M. Shoji, S. Kishida, Y. Hayashi, T. Kataoka, H. Osada, Bioorg. Med. Chem. Lett. 2003, 13, 3743.
    • The preliminary results have been published. H. Kakeya, Y. Miyake, M. Shoji, S. Kishida, Y. Hayashi, T. Kataoka, H. Osada, Bioorg. Med. Chem. Lett. 2003, 13, 3743.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.