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Short Note

8,9-24,25-Diepoxy-Eupho-lanostan-3,4-olactone

by
N. El Aouad
1,*,
A. Benharref
1 and
J.-P. Lavergne
2
1
Laboratoire de Chimie des Substances Naturelles et des Hétérocycles, Université Cadi Ayaad, Faculté des Sciences Semlalia, Marrakech. Maroc
2
Laboratoire des Aminoacides, Peptides et Protéines, Université Montpellier II, 34095- Montpellier cedex 5. France
*
Author to whom correspondence should be addressed.
Molecules 2000, 5(12), M172; https://doi.org/10.3390/M172
Submission received: 4 July 2000 / Accepted: 21 July 2000 / Published: 25 December 2000
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Versions Notes
Molecules 05 m172 i001
To a mixture of 0.8 g (4.7 mmol) of metachloroperbenzoique acid (mCPBA) and 1.58g (18.8mmol) of sodium hydrogenocarbonate (NaHCO3) in 15 ml of dichloromethane was added 1 g (2.35 mmol) of 1 in 5 ml of CH2Cl2. After being stirred for 18h, the mixture was washed with 20 ml of 10% Na2CO3 and then 20 ml of saturated NaHCO3. The organic layer was dried over Na2SO4 and concentrated in vacuum. The yellow residue was purified by silica gel column chromatography using 85 : 15 hexane : ethyl acetate as eluant to give 2 (540 mg, 48.5%).
Mp: 146-148°C.
IR: 1746.
MS: [M+H]+ = 473.
1H NMR (250 MHz, CDCl3): 2.5 (m, C2-H2); 0.75 (s, C18- H3); 0.87 (s, C19-H3); 0.95 (d, J= 6Hz, C21-H3); 2.65 (t, J=10Hz, C24-H); 1.25 (s, C26-H3); 1.27 (s, C27-H3); 0.79 (s, C28-H3); 1.3 (s, C29-H3); 1.32 (s, C30-H3).
13C NMR (62.5 MHz, CDCl3):35.2 (C1); 36.8 (C2); 175.73 (C3); 85.5 (C4); 50.9 (C5); 18.8 (C6); 28.0 (C7); 68.65 (C8); 69.7 (C9); 37.2 (C10); 21.4 (C11); 28.2 (C12); 44.0 (C13); 49.6 (C14); 30.7 (C15); 29.7 (C16); 47.7 (C17); 15.5 (C18); 20.1 (C19); 35.4 (C20); 18.5 (C21); 35.7 (C22); 30.8 (C23); 49.42 (C24); 58.52 (C25); 24.9 (C26); 24.6(C27); 24.4(C28); 27.9(C29); 15.7(C30).

References

  1. Benharref, A.; Lavergne, J.-P. Bull. Soc. Chim. Fr. 1985, 965.
  2. Kenneth, B. W.; John, R. S. J. Org. Chem. 1998, 63, 1390–1401.
Sample Availability: Available from the authors and from MDPI.

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MDPI and ACS Style

Aouad, N.E.; Benharref, A.; Lavergne, J.-P. 8,9-24,25-Diepoxy-Eupho-lanostan-3,4-olactone. Molecules 2000, 5, M172. https://doi.org/10.3390/M172

AMA Style

Aouad NE, Benharref A, Lavergne J-P. 8,9-24,25-Diepoxy-Eupho-lanostan-3,4-olactone. Molecules. 2000; 5(12):M172. https://doi.org/10.3390/M172

Chicago/Turabian Style

Aouad, N. El, A. Benharref, and J.-P. Lavergne. 2000. "8,9-24,25-Diepoxy-Eupho-lanostan-3,4-olactone" Molecules 5, no. 12: M172. https://doi.org/10.3390/M172

APA Style

Aouad, N. E., Benharref, A., & Lavergne, J.-P. (2000). 8,9-24,25-Diepoxy-Eupho-lanostan-3,4-olactone. Molecules, 5(12), M172. https://doi.org/10.3390/M172

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