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Natural Product Letters Volume 5, 1994 - Issue 1
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Original Articles

Transformation of Labdanes into Drimanes. Semisyntheses of Poligodial and Warburganal from Zamoranic Acid

Julio G. Urones Departamento de Química Orgánica, Facultadde Ciencias Químicas, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008, Salamanca, SPAIN Fax:
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Isidro S. Marcos Departamento de Química Orgánica, Facultadde Ciencias Químicas, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008, Salamanca, SPAIN Fax:
,
Belen Gomez Perez Departamento de Química Orgánica, Facultadde Ciencias Químicas, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008, Salamanca, SPAIN Fax:
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Anna M. Lithgow Departamento de Química Orgánica, Facultadde Ciencias Químicas, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008, Salamanca, SPAIN Fax:
,
David Diez Departamento de Química Orgánica, Facultadde Ciencias Químicas, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008, Salamanca, SPAIN Fax:
,
Pilar Basabe Departamento de Química Orgánica, Facultadde Ciencias Químicas, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008, Salamanca, SPAIN Fax:
&
Patricio M. Gomez Departamento de Química Orgánica, Facultadde Ciencias Químicas, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008, Salamanca, SPAIN Fax:
show all
Pages 21-24 | Received 31 May 1994, Published online: 04 Oct 2006

References

  • de Pascual Teresa , J. , Urones , J. G. , Marcos , I. S. , Díez Martín , D. and Álvarez Monje , V. 1986 . Phytochemistry , 25 : 711
  • Jansen , B. M. J. and de Groot , Æ. 1991 . Nat. Prod. Rep. , 8 : 309
  • Jansen , B. M.J. and de Groot , Æ. 1991 . Nat. Prod. Rep. , 8 : 319
  • Barnes , C. S. and Loder , J. W. 1962 . Aust. J. Chem. , 15 : 322
  • Kubo , I. , Lee , Y. -W. , Pettei , M. , Pilkiewicz , F. and Nakanishi , K. 1976 . J. Chem. Soc. Chem. Commun. , 1013
  • Full experimental details will be discussed elsewhere
  • [α]D 22 = – 75.2° (CHCl3, c 2.8), UV (EtOH) λmax nm: 219 (ε 21000) IR vmax cm−1: 3080, 1725, 1645, 1240, 1160, 905, 790. EIMS (rel. int.): 248 (M+, 41), 233(15), 217(13), 205(14), 179(18), 163(16), 149(25), 133(15), 119(28), 105(33), 91(41), 81(49), 69(100). 1H NMR δ (ppm): 6.69 (1H, m, H-7), 5.32 (1H, s, Ha-11), 5.09 (1H, s, Hb-11), 3.77 (3H, s, ‒CO2Me), 2.31 (1H, dt, J = 20.0 and 5.4 Hz, Ha–6), 2.14 (1H, ddd, J = 20.0, 11.7 and 2.9 Hz, Hb-6), 0.98, 0.93, 0.87 (3H, s, ea, Me–15, Me–14 and Me–13). 13C NMR δ (ppm, carbon number): 37.3(1), 18.9(2), 42.2(3), 33.4(4), 47.8(5), 24.7(6), 137.5(7), 131.1(8), 151.3(9), 37.9(10), 108.8(11), 168.4(12), 32.7(13), 21.9(14), 20.2(15), 51.6 (‒CO2Me)
  • IR vmax cm−1: 1730, 1650, 1450, 1250, 1160, 1050, 825. EIMS (rel. int.): 264 (M+, 72), 249(10), 219(100), 109(32), 91(38), 69(33), 55(40). 1H NMR δ (ppm): 7.20 (1H, m, H-7), 3.75 (1H, d, J = 4.4 Hz, Ha- 11), 3.70 (3H, s, ‒CO2Me), 2.94 (1H, d, J=4.4 Hz, Hb-11), 1.00, 0.93, 0.91 (3H, s, ea). 13C NMR δ (ppm, carbon number): 29.9(1), 18.0(2), 41.5(3), 33.1(4), 45.1(5), 25.0(6), 146.6(7), 128.7(8), 61.6(9), 36.5(10), 49.4(11), 167.2(12), 32.4(13), 21.7(14), 18.4(15), 51.6 (‒CO2Me)
  • Hanson , R. M. 1984 . Tetrahedron Lett. , 25 : 3783
  • Blackett , B. N. , Coxon , J. M. , Hartshorn , M. P. , Jacksonand , B. L.J. and Muir , C. N. 1969 . Tetrahedron , 25 : 1479
  • Blackett , B. N. , Coxon , J. M. , Hartshorn , M. P. and Richards , K. E. 1970 . J. Am. Chem. Soc. , 72 : 2574
  • IR vmax cm−1: 2710, 1720, 1710, 1660, 1250, 1150, 860. EIMS (rel. int.): 264 (M+, 2), 236(70), 221(20), 177(10), 124(68), 109(100), 91(55), 81(38), 69(58), 55(57). 1H NMR δ (ppm): 9.53 (1H, d, J = 3.9 Hz), 7.23 (1H, m, H-7), 3.71 (3H, s, ‒CO2Me), 2.92 (1H, m, H–9), 0.93 (6H, s), 0.90 (3H, s). 13C NMR δ (ppm, carbon number): 39.7(1), 18.1(2), 41.9(3), 33.2(4), 48.7(5), 24.4(6), 143.0(7), 127.1(8), 62.2(9), 37.1(10), 202.0(11), 167.3(12), 33.0(13), 21.9(14), 15.2(15), 51.7 (‒CO2Me)
  • Mori , K. and Watanabe , H. 1986 . Tetrahedron , 42 : 273
  • Hollinshead , D. M. , Howell , S. C. , Ley , S. V. , Mahon , M. , Ratcliffe , N. M. and Worthington , P. A. 1983 . J. Chem. Soc. Perkin Trans. I , 1579

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