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Molbank 2006, M507 |
3¦Â-Tosyloxy-elemo-lanost-8-en-24-one
Noureddine Mazoir,* Mourad Daoubi, Essediya Lassaba and Ahmed Benharref
Laboratoire de Chimie des Substances Naturelles, Universit¨¦ Cadi
Ayyad, Facult¨¦ des Sciences Semlalia, B.P: 2390. Marrakech. Maroc.
E-mail: [email protected]
*Author to whom correspondence should be
addressed
Received: 1 August 2005 / Accepted: 17
October 2006 / Published: 1 December 2006
Keywords: latex, Euphorbia resinifera, ruthenium trichloride.
The sodium periodate is prepared in
situ with equimolecular quantity of soda NaOH (0.5g; 12.50 mmol) and periodic
acid H5IO6 (2.85g; 12.50 mmol), the mixture is stirred at
0¡ãC. After 15 min, 5 ml of CCl4, 5 ml of H3CCN and
93.03mg (0.12mmol) of ruthenium trichloride1,2 were added. The
mixture was stirred during 15min, and then 1.85g (3.12 mmol) of 13 was added. The
reaction was left under stirring at 25¡ãC for 30h, then 20 ml of distilled water
was added and the reactional mixture was extracted with the dichloromethane.
After filtration on silica gel column to eliminate RuO4, the organic
layer was recovered, dried by Na2SO4 and evaporated under
reduce pressure. The residue was purified on silica gel column using hexane:
ethyl acetate (96: 4) as eluent to give 1.30g (2.18 mmol) of 2 in 70 % yield.
Melting point: 115-116
¡ãC (Hexane)
MS (EI, 70eV): 596 (M+.).
1H NMR
(300 MHz, CDCl3) d(ppm): 4.22 (1H-3, dd, J1 = 12 Hz, J2
= 4 Hz ); 7.96 (2H-2¡¯, d, J = 8.8Hz); 7.35 (2H-3¡¯, d, J = 8.8 Hz); 2.48
(3H-5¡¯); 0.76 (3H-18, s); 0.85
(3H-19, s); 0.93 (3H-21, d, J = 6 Hz); 2.60 (2H-23, m); 1.10 (3H-26, d: J = 2
Hz); 1.11 (3H-27, d, J = 2 Hz); 0.80 (3H-28, s); 0.95 (3H-29, s); 1.05 (3H-30,
s).
13C NMR (75 MHz, CDCl3)d (ppm): 35.15 (C-1); 27.52 (C-2);
91.00 (C-3); 36.25 (C-4); 49.98 (C-5); 38.78 (C-6); 28.03 (C-7); 133.66 (C-8);
134.93 (C-9); 36.25 (C-10); 20.20 (C-11); 25.47 (C-12); 44.16 (C-13); 50.16
(C-14); 30.76 (C-15); 30.21 (C-16); 51.33 (C-17); 18.64 (C-18); 18.99 (C-19);
37.01 (C-20); 21.54 (C-21); 37.59 (C-22); 29.84 (C-23); 215.50 (C-24); 35.64
(C-25); 21.72 (C-26); 22.40 (C-27); 31.80 (C-25); 21.70 (C-26); 18.80 (C-27);
14.5 (C-28); 16.41 (C-29); 144.35 (C-1¡¯); 129.76 (C-2¡¯); 127.77 (C-3¡¯); 134.82
(C-4¡¯); 21.25 (C-5¡¯).
MS (m/z): 596 (35%), 425 (48%), 297 (75%).
Acknowledgments
We would like to thank Pr. A. Idmessaaoud for helpful discussions.
References
1. Gore, E. S. Platinum Met. Rev. 1983, 27, 111.
2.
Mazoir, N.; Giorgi, M and Auhmani, A. Acta
Cryst. 2005, E61, o2382-2383.
3. Mazoir, N.; Auhmani, A.; Dakir, M. ; Ait Itto, My. Y and Benharref, A. Molbank. 2004, M366.
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