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Natural Product Letters Volume 5, 1994 - Issue 3
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Original Articles

Highly Regioselective Elimination of a Ring—attached Acetoxy Group: Methyl Ent—Isocopalate from Sclareol

Julio G. Urones Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008, Salamanca, SPAIN Fax:
,
Isidro S. Marcos Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008, Salamanca, SPAIN Fax:
,
Pilar Basabe Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008, Salamanca, SPAIN Fax:
,
Antonio Gomez Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008, Salamanca, SPAIN Fax:
,
Antonio Estrella Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008, Salamanca, SPAIN Fax:
&
Anna M. Lithgow Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008, Salamanca, SPAIN Fax:
Pages 217-220 | Received 16 Sep 1994, Published online: 04 Oct 2006

References

  • Cimino , G. , de Rosa , D. , de Stefano , S. and Minale , L. 1974 . Tetrahedron , 30 : 645
  • Faulkner , D. J. 1984 . Nat. Prod. Rep. , 1 : 251 Nat. Prod. Rep. (1984) 1, 551; Nat. Prod. Rep. (1986) 3, 1; Nat. Prod. Rep. (1987) 4, 539; Nat. Prod. Rep. (1988) 5, 613; Nat. Prod. Rep. (1990) 7, 269; Nat. Prod. Rep. (1991) 8, 97
  • Imamura , P. M. , Sierra , M. G. and Rúveda , E. 1981 . J.C.S. Chem. Commun. , 734
  • Overman , L. E. and Knoll , F. M. 1979 . Tetrahedron Lett. , 4 : 321
  • A typical procedure is as follows: To a solution of 2 (5.3 g, 13.5 mmol) in THF (21 ml) was added 172 mg PdCl2(CH3CN)2. The mixture was stirred at room temperature under Ar atmosphere for 3.5 h. Then hexane was added, the solution filtered and the solvent removed in vacuo. Column chromatography of the crude product eluting with hexane/EtOAc 9:1 afforded 3 (10%) and 4 (89%)
  • Mancuso , A. J. and Swern , D. 1981 . Synthesis , 165
  • Balkrishna , S. B. , Childers , W. E. and Pinnick , W. H. 1981 . Tetrahedron , 37 : 2091
  • The general procedure is as follows: To a solution of the methyl ester 7 in hexane was added SiO2 (Merck 600.2–0.63 mm, 10:1, with respect to the substrate). The mixture was shaken at 100°C for 45 min. The reaction was monitored by TLC by suspension of a little portion of the mixture in 0.5 ml of solvent). When the reaction was complete, the product was extracted from SiO2 eluting with hexane
  • Bory , S. , Fétizon , M. and Laszlo , P. 1963 . Bull. Soc. Chim. France , 2310
  • All compounds exhibited IR, 1H and 13C NMR spectra in agreement with the assigned structures. Properties of 6: IR νmax cm−1: 2700, 1730, 1680, 1630, 1240, 1130 and 1020. 1H NMR δ (ppm): 8.60 (1H, d, J, = 7.0 Hz, H–15); 5.89 (1H, d, J, = 7.0 Hz, H–14); 2.18 (3H, s, Me–16); 1.93 (3H, s, MeCO2); 1.46 (3H, s, Me–17); 0.78 (3H, s, Me–19); 0.66 (3H, s, Me–18); 0.63 (3H, s, Me–20). 13C NMR δ (ppm, carbon number): 39.8(1), 18.4(2), 41.9(3), 33.2(4), 55.8(5), 20.0(6), 38.9(7), 88.0(8), 58.7(9), 39.6(10), 24.0(11), 43.6(12), 164.1(13), 127.1(14), 191.1(15), 17.7(16), 22.8(17), 33.3(18), 20.6(19), 15.7(20), 169.8 (MeCOO), 21.4 (MeCOO)

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