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Volumn , Issue 8, 2002, Pages 395-397

Highly efficient synthesis of the optically active sesquiterpene hydroquinone (+)-zonarol and the sesquiterpene quinone (+)-zonarone

Author keywords

Drimane; Sesquiterpene; Sesquiterpene hydroquinone; Sesquiterpene quinone

Indexed keywords

HYDROQUINONE DERIVATIVE; QUINONE DERIVATIVE; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG; ZONAROL; ZONARONE;

EID: 0036697733     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.3184/030823402103172437     Document Type: Article
Times cited : (9)

References (25)
  • 2
    • 0026756956 scopus 로고
    • J. Rodriguez, E. Quiñoa, R. Riguera, B.M. Peters, L.M. Abrell and P. Crews, Tetrahedron, 1992, 48, 6667; R. Talpir, A. Rudi, Y. Kashman, Y. Loya and A. Hizi, Tetrahedron, 1994, 50, 4179; S.J. Coval, M.A. Conover, R. Mierzwa, A. King, M.S. Puar, D.W. Phife, J.-K. Pai, R.E. Burrier, M.-S. Ahn, G.C. Boykov, M. Patel, S.A. Pomponi, Bio. Med. Chem. Lett. 1995, 5, 605; S. Chackalamannil, Y. Xia, Y. Wang, M. Tsai, M. Czarniecki, S. Nang, A. Clemmons, H.S. Ahn, G. Boykov, Biol. Med. Chem. Lett. 1995, 5, 2005; S. Urban and R.J. Capon, Aust. J. Chem., 1996, 49, 611; M.A. Belisario, M. Maturo, G. Avagnale, S. De Rosa, F. Scopacasa and M. De Caterina, Pharmacol. Toxicol., 1996, 79, 300.
    • (1992) Tetrahedron , vol.48 , pp. 6667
    • Rodriguez, J.1    Quiñoa, E.2    Riguera, R.3    Peters, B.M.4    Abrell, L.M.5    Crews, P.6
  • 3
    • 0028348152 scopus 로고
    • J. Rodriguez, E. Quiñoa, R. Riguera, B.M. Peters, L.M. Abrell and P. Crews, Tetrahedron, 1992, 48, 6667; R. Talpir, A. Rudi, Y. Kashman, Y. Loya and A. Hizi, Tetrahedron, 1994, 50, 4179; S.J. Coval, M.A. Conover, R. Mierzwa, A. King, M.S. Puar, D.W. Phife, J.-K. Pai, R.E. Burrier, M.-S. Ahn, G.C. Boykov, M. Patel, S.A. Pomponi, Bio. Med. Chem. Lett. 1995, 5, 605; S. Chackalamannil, Y. Xia, Y. Wang, M. Tsai, M. Czarniecki, S. Nang, A. Clemmons, H.S. Ahn, G. Boykov, Biol. Med. Chem. Lett. 1995, 5, 2005; S. Urban and R.J. Capon, Aust. J. Chem., 1996, 49, 611; M.A. Belisario, M. Maturo, G. Avagnale, S. De Rosa, F. Scopacasa and M. De Caterina, Pharmacol. Toxicol., 1996, 79, 300.
    • (1994) Tetrahedron , vol.50 , pp. 4179
    • Talpir, R.1    Rudi, A.2    Kashman, Y.3    Loya, Y.4    Hizi, A.5
  • 4
    • 0028955337 scopus 로고
    • J. Rodriguez, E. Quiñoa, R. Riguera, B.M. Peters, L.M. Abrell and P. Crews, Tetrahedron, 1992, 48, 6667; R. Talpir, A. Rudi, Y. Kashman, Y. Loya and A. Hizi, Tetrahedron, 1994, 50, 4179; S.J. Coval, M.A. Conover, R. Mierzwa, A. King, M.S. Puar, D.W. Phife, J.-K. Pai, R.E. Burrier, M.-S. Ahn, G.C. Boykov, M. Patel, S.A. Pomponi, Bio. Med. Chem. Lett. 1995, 5, 605; S. Chackalamannil, Y. Xia, Y. Wang, M. Tsai, M. Czarniecki, S. Nang, A. Clemmons, H.S. Ahn, G. Boykov, Biol. Med. Chem. Lett. 1995, 5, 2005; S. Urban and R.J. Capon, Aust. J. Chem., 1996, 49, 611; M.A. Belisario, M. Maturo, G. Avagnale, S. De Rosa, F. Scopacasa and M. De Caterina, Pharmacol. Toxicol., 1996, 79, 300.
    • (1995) Bio. Med. Chem. Lett. , vol.5 , pp. 605
    • Coval, S.J.1    Conover, M.A.2    Mierzwa, R.3    King, A.4    Puar, M.S.5    Phife, D.W.6    Pai, J.-K.7    Burrier, R.E.8    Ahn, M.-S.9    Boykov, G.C.10    Patel, M.11    Pomponi, S.A.12
  • 5
    • 0029125526 scopus 로고
    • J. Rodriguez, E. Quiñoa, R. Riguera, B.M. Peters, L.M. Abrell and P. Crews, Tetrahedron, 1992, 48, 6667; R. Talpir, A. Rudi, Y. Kashman, Y. Loya and A. Hizi, Tetrahedron, 1994, 50, 4179; S.J. Coval, M.A. Conover, R. Mierzwa, A. King, M.S. Puar, D.W. Phife, J.-K. Pai, R.E. Burrier, M.-S. Ahn, G.C. Boykov, M. Patel, S.A. Pomponi, Bio. Med. Chem. Lett. 1995, 5, 605; S. Chackalamannil, Y. Xia, Y. Wang, M. Tsai, M. Czarniecki, S. Nang, A. Clemmons, H.S. Ahn, G. Boykov, Biol. Med. Chem. Lett. 1995, 5, 2005; S. Urban and R.J. Capon, Aust. J. Chem., 1996, 49, 611; M.A. Belisario, M. Maturo, G. Avagnale, S. De Rosa, F. Scopacasa and M. De Caterina, Pharmacol. Toxicol., 1996, 79, 300.
    • (1995) Biol. Med. Chem. Lett. , vol.5 , pp. 2005
    • Chackalamannil, S.1    Xia, Y.2    Wang, Y.3    Tsai, M.4    Czarniecki, M.5    Nang, S.6    Clemmons, A.7    Ahn, H.S.8    Boykov, G.9
  • 6
    • 0000390494 scopus 로고    scopus 로고
    • J. Rodriguez, E. Quiñoa, R. Riguera, B.M. Peters, L.M. Abrell and P. Crews, Tetrahedron, 1992, 48, 6667; R. Talpir, A. Rudi, Y. Kashman, Y. Loya and A. Hizi, Tetrahedron, 1994, 50, 4179; S.J. Coval, M.A. Conover, R. Mierzwa, A. King, M.S. Puar, D.W. Phife, J.-K. Pai, R.E. Burrier, M.-S. Ahn, G.C. Boykov, M. Patel, S.A. Pomponi, Bio. Med. Chem. Lett. 1995, 5, 605; S. Chackalamannil, Y. Xia, Y. Wang, M. Tsai, M. Czarniecki, S. Nang, A. Clemmons, H.S. Ahn, G. Boykov, Biol. Med. Chem. Lett. 1995, 5, 2005; S. Urban and R.J. Capon, Aust. J. Chem., 1996, 49, 611; M.A. Belisario, M. Maturo, G. Avagnale, S. De Rosa, F. Scopacasa and M. De Caterina, Pharmacol. Toxicol., 1996, 79, 300.
    • (1996) Aust. J. Chem. , vol.49 , pp. 611
    • Urban, S.1    Capon, R.J.2
  • 7
    • 0030457943 scopus 로고    scopus 로고
    • J. Rodriguez, E. Quiñoa, R. Riguera, B.M. Peters, L.M. Abrell and P. Crews, Tetrahedron, 1992, 48, 6667; R. Talpir, A. Rudi, Y. Kashman, Y. Loya and A. Hizi, Tetrahedron, 1994, 50, 4179; S.J. Coval, M.A. Conover, R. Mierzwa, A. King, M.S. Puar, D.W. Phife, J.-K. Pai, R.E. Burrier, M.-S. Ahn, G.C. Boykov, M. Patel, S.A. Pomponi, Bio. Med. Chem. Lett. 1995, 5, 605; S. Chackalamannil, Y. Xia, Y. Wang, M. Tsai, M. Czarniecki, S. Nang, A. Clemmons, H.S. Ahn, G. Boykov, Biol. Med. Chem. Lett. 1995, 5, 2005; S. Urban and R.J. Capon, Aust. J. Chem., 1996, 49, 611; M.A. Belisario, M. Maturo, G. Avagnale, S. De Rosa, F. Scopacasa and M. De Caterina, Pharmacol. Toxicol., 1996, 79, 300.
    • (1996) Pharmacol. Toxicol. , vol.79 , pp. 300
    • Belisario, M.A.1    Maturo, M.2    Avagnale, G.3    De Rosa, S.4    Scopacasa, F.5    De Caterina, M.6
  • 8
    • 0030729376 scopus 로고    scopus 로고
    • (a) A.F. Barrero, E.J. Alvarez-Manzaneda and R. Chahboun, Tetrahedron Lett., 1997, 38, 8101; A.F. Barrero, E.J. Alvarez-Manzaneda and R. Chahboun, Tetrahedron, 1998, 54, 5635; A.F. Barrero, E.J. Alvarez-Manzaneda, M. Mar Herrador, R. Chahboun and P. Galera, Bioorg. Med. Lett., 1999, 9, 2325; S.C. Welch, A.S.C.P. Rao, Tetrahedron Lett., 1977, 505; S.C. Welch, A.S.C.P. Rao, J. Org. Chem., 1978, 43, 1957; K. Mori and M. Komatsu, Bull. Soc. Chim. Belg, 1986, 95, 771; H. Akita, M. Nozawa and H. Shimizu, Tetrahedron: Asym. 1998, 1, 1789;
    • (1997) Tetrahedron Lett. , vol.38 , pp. 8101
    • Barrero, A.F.1    Alvarez-Manzaneda, E.J.2    Chahboun, R.3
  • 9
    • 0032554838 scopus 로고    scopus 로고
    • (a) A.F. Barrero, E.J. Alvarez-Manzaneda and R. Chahboun, Tetrahedron Lett., 1997, 38, 8101; A.F. Barrero, E.J. Alvarez-Manzaneda and R. Chahboun, Tetrahedron, 1998, 54, 5635; A.F. Barrero, E.J. Alvarez-Manzaneda, M. Mar Herrador, R. Chahboun and P. Galera, Bioorg. Med. Lett., 1999, 9, 2325; S.C. Welch, A.S.C.P. Rao, Tetrahedron Lett., 1977, 505; S.C. Welch, A.S.C.P. Rao, J. Org. Chem., 1978, 43, 1957; K. Mori and M. Komatsu, Bull. Soc. Chim. Belg, 1986, 95, 771; H. Akita, M. Nozawa and H. Shimizu, Tetrahedron: Asym. 1998, 1, 1789;
    • (1998) Tetrahedron , vol.54 , pp. 5635
    • Barrero, A.F.1    Alvarez-Manzaneda, E.J.2    Chahboun, R.3
  • 10
    • 0033575715 scopus 로고    scopus 로고
    • (a) A.F. Barrero, E.J. Alvarez-Manzaneda and R. Chahboun, Tetrahedron Lett., 1997, 38, 8101; A.F. Barrero, E.J. Alvarez-Manzaneda and R. Chahboun, Tetrahedron, 1998, 54, 5635; A.F. Barrero, E.J. Alvarez-Manzaneda, M. Mar Herrador, R. Chahboun and P. Galera, Bioorg. Med. Lett., 1999, 9, 2325; S.C. Welch, A.S.C.P. Rao, Tetrahedron Lett., 1977, 505; S.C. Welch, A.S.C.P. Rao, J. Org. Chem., 1978, 43, 1957; K. Mori and M. Komatsu, Bull. Soc. Chim. Belg, 1986, 95, 771; H. Akita, M. Nozawa and H. Shimizu, Tetrahedron: Asym. 1998, 1, 1789;
    • (1999) Bioorg. Med. Lett. , vol.9 , pp. 2325
    • Barrero, A.F.1    Alvarez-Manzaneda, E.J.2    Mar Herrador, M.3    Chahboun, R.4    Galera, P.5
  • 11
    • 49349138101 scopus 로고
    • (a) A.F. Barrero, E.J. Alvarez-Manzaneda and R. Chahboun, Tetrahedron Lett., 1997, 38, 8101; A.F. Barrero, E.J. Alvarez-Manzaneda and R. Chahboun, Tetrahedron, 1998, 54, 5635; A.F. Barrero, E.J. Alvarez-Manzaneda, M. Mar Herrador, R. Chahboun and P. Galera, Bioorg. Med. Lett., 1999, 9, 2325; S.C. Welch, A.S.C.P. Rao, Tetrahedron Lett., 1977, 505; S.C. Welch, A.S.C.P. Rao, J. Org. Chem., 1978, 43, 1957; K. Mori and M. Komatsu, Bull. Soc. Chim. Belg, 1986, 95, 771; H. Akita, M. Nozawa and H. Shimizu, Tetrahedron: Asym. 1998, 1, 1789;
    • (1977) Tetrahedron Lett. , pp. 505
    • Welch, S.C.1    Rao, A.S.C.P.2
  • 12
    • 0017886274 scopus 로고
    • (a) A.F. Barrero, E.J. Alvarez-Manzaneda and R. Chahboun, Tetrahedron Lett., 1997, 38, 8101; A.F. Barrero, E.J. Alvarez-Manzaneda and R. Chahboun, Tetrahedron, 1998, 54, 5635; A.F. Barrero, E.J. Alvarez-Manzaneda, M. Mar Herrador, R. Chahboun and P. Galera, Bioorg. Med. Lett., 1999, 9, 2325; S.C. Welch, A.S.C.P. Rao, Tetrahedron Lett., 1977, 505; S.C. Welch, A.S.C.P. Rao, J. Org. Chem., 1978, 43, 1957; K. Mori and M. Komatsu, Bull. Soc. Chim. Belg, 1986, 95, 771; H. Akita, M. Nozawa and H. Shimizu, Tetrahedron: Asym. 1998, 1, 1789;
    • (1978) J. Org. Chem. , vol.43 , pp. 1957
    • Welch, S.C.1    Rao, A.S.C.P.2
  • 13
    • 0022994556 scopus 로고
    • (a) A.F. Barrero, E.J. Alvarez-Manzaneda and R. Chahboun, Tetrahedron Lett., 1997, 38, 8101; A.F. Barrero, E.J. Alvarez-Manzaneda and R. Chahboun, Tetrahedron, 1998, 54, 5635; A.F. Barrero, E.J. Alvarez-Manzaneda, M. Mar Herrador, R. Chahboun and P. Galera, Bioorg. Med. Lett., 1999, 9, 2325; S.C. Welch, A.S.C.P. Rao, Tetrahedron Lett., 1977, 505; S.C. Welch, A.S.C.P. Rao, J. Org. Chem., 1978, 43, 1957; K. Mori and M. Komatsu, Bull. Soc. Chim. Belg, 1986, 95, 771; H. Akita, M. Nozawa and H. Shimizu, Tetrahedron: Asym. 1998, 1, 1789;
    • (1986) Bull. Soc. Chim. Belg. , vol.95 , pp. 771
    • Mori, K.1    Komatsu, M.2
  • 14
    • 0032557717 scopus 로고    scopus 로고
    • (a) A.F. Barrero, E.J. Alvarez-Manzaneda and R. Chahboun, Tetrahedron Lett., 1997, 38, 8101; A.F. Barrero, E.J. Alvarez-Manzaneda and R. Chahboun, Tetrahedron, 1998, 54, 5635; A.F. Barrero, E.J. Alvarez-Manzaneda, M. Mar Herrador, R. Chahboun and P. Galera, Bioorg. Med. Lett., 1999, 9, 2325; S.C. Welch, A.S.C.P. Rao, Tetrahedron Lett., 1977, 505; S.C. Welch, A.S.C.P. Rao, J. Org. Chem., 1978, 43, 1957; K. Mori and M. Komatsu, Bull. Soc. Chim. Belg, 1986, 95, 771; H. Akita, M. Nozawa and H. Shimizu, Tetrahedron: Asym. 1998, 1, 1789;
    • (1998) Tetrahedron: Asym. , vol.1 , pp. 1789
    • Akita, H.1    Nozawa, M.2    Shimizu, H.3
  • 17
    • 0001623106 scopus 로고
    • ed. Atta-ur-Rahman, Elsevier, Amsterdam and refs cited therein
    • T. Nakano, in Studies in Natural Products Chemistry, ed. Atta-ur-Rahman, Elsevier, Amsterdam, 1989, vol 4, p. 403 and refs cited therein; J. Villamizar, Rev. Latinoamer. Quim., 1999, 27, 96.
    • (1989) Studies in Natural Products Chemistry , vol.4 , pp. 403
    • Nakano, T.1
  • 18
    • 0010676662 scopus 로고    scopus 로고
    • T. Nakano, in Studies in Natural Products Chemistry, ed. Atta-ur-Rahman, Elsevier, Amsterdam, 1989, vol 4, p. 403 and refs cited therein; J. Villamizar, Rev. Latinoamer. Quim., 1999, 27, 96.
    • (1999) Rev. Latinoamer. Quim. , vol.27 , pp. 96
    • Villamizar, J.1


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