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8a,13-Epoxy-14,15-dinorlabd-12-ene (Sclareol Oxide) [(+)-(4aR,6aS,10aS,10bR)-3,4a,7,7,10a-Pentamethyl-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-1H-benzo[f]chromene]

Departamento de Química Inorgánica y Orgánica, Facultad de Ciencias Experimentales, Universidad de Jaén, 23071 Jaén, Spain
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Author to whom correspondence should be addressed.
Molbank 2003, 2003(1), M304; https://doi.org/10.3390/M304
Received: 12 December 2001 / Accepted: 19 September 2002 / Published: 8 March 2003
Keywords: Diterpenes; labdanes; sclareol oxide; cleavage of alkenes; potassium permanganate; cyclic enol ether Diterpenes; labdanes; sclareol oxide; cleavage of alkenes; potassium permanganate; cyclic enol ether
Molbank 2003 m304 i001
To a stirred solution of a mixture of E/Z isomers 1 (174 mg, 0.52 mmol, 45:55 ratio) in acetone (8 mL) was added a mixture of KMnO4 (260 mg, 1.64 mmol) and anhydrous MgSO4 (230 mg) at 10 °C [1]. After stirring for 10 min the reaction was allowed to warm to room temperature. After 20 min more the crude was filtered over Celite and the clean solution evaporated under reduced pressure to yield a residue which was solved in Et2O (25 mL). This solution was washed with brine (3×10 mL), dried over anhydrous Na2SO4 and the solvent evaporated under reduced pressure to yield a residue (128 mg) which was solved in toluene (10 mL) and distilled in a Dean-Stark trap device for 1 h. The resulting solution was evaporated under reduced presure to yield the title compound 2 (120 mg, 0.46 mmol, 88%).
Mp: 34.0-36.0 °C (white crystals, from methanol).
[a]D = +1.22° (c 0.95 cg·mL-1, CHCl3).
IR (neat, n, cm-1): 3054, 1683 (C=C), 1127 (C-O-C).
1H NMR (300 MHz, CDCl3, d, ppm): 0.82 (6H, s, Meb-4, Me-10), 0.88 (3H, s, Mea-4), 1.16 (3H, s, Me-8), 1.68 (3H, br s, Me-13), 0.89-1.85 (13H, m, H-1,2,3,5,6,7a,9,11), 1.94 (1H, dt, J=12.3 Hz, 3.2 Hz, Hb-7), 4.43 (1H, br s, H-12).
13C NMR (75 MHz, CDCl3, d, ppm): 39.29 (C-1), 18.56 (C-2), 41.91 (C-3), 33.14 (C-4), 56.17 (C-5), 19.74 (C-6), 41.12 (C-7), 76.17 (C-8), 52.43 (C-9), 36.66 (C-10), 18.26 (C-11), 94.54 (C-12), 147.83 (C-13), 20.43 (C-16), 20.07 (C-17), 33.43 (C-18), 21.55 (C-19), 15.00 (C-20).

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgements

We wish to thank the Junta de Andalucía for financial support and the Ministerio de Educación, Cultura y Deporte for a Fellowship to J. M. Castro.

References and Notes

  1. Leite, M. A. F.; Sarragiotto, M. H.; Imamura, P. M.; Marsaioli, A. J. Absolute Configuration of Drim-9(11)-en-8-ol from Aspergillus oryzae. J. Org. Chem. 1986, 51, 5409–5410. [Google Scholar] [CrossRef]
  • Sample availability: Available from the authors and from MDPI
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