(1S,4R,5R,8R,9S,12R,13S),12-(1S-hydroxyethyl)-13-(N-benzyl-2-carboxamido ethyl)-5-(1,5-dimethylhexyl)-1,9-epoxy-4,8,13-trimethyl tricyclo [7,4,0,04,8]

Molecules 2001, 6, M222

(1S,4R,5R,8R,9S,12R,13S),12-(1S-Hydroxyethyl)-13-(N-benzyl-2-carboxamido Ethyl)-5-(1,5-dimethylhexyl)-1,9-epoxy-4,8,13-trimethyl Tricyclo [7,4,0,0,4,8] Tridecane

M. Daoubi¹, A. Benharref¹ and Diego. M. Cortes²

1. Laboratoire de Chimie des Substances Naturelles et des Hétérocycles, Université Cadi Ayyad, Faculté des Sciences SemLalia, BP 2390. Bd Prince My Abdellah, Marrakech. Maroc. E-mail : [email protected]
2 . Departamento de Farmacologia, Laboratorio deFarmacognosia y Farmacodinamia, Universidad de Valencia, Facultad des Farmacia, Av. Vincent Andrés Estellés s/n, 46100 BURJASSOT (velencia) Spain

Received: 19 February 2001 / Accepted: 15 May 2001 / Published: 25 May 2001

A mixture 1 [1] (1 g, 2.25 mmol) and benzylamine [2] as a solvent was refluxed for 3 hours. After being cooled at room temperature, the excess amount of benzylamine was removed under reduced pressure, and the residue was chromatographed (silica gel, Hexane-EtOAc, 75 : 25) to give 2 (1.12 g, 96 %).

Mp: 135-136 °C.

MS (EI, 70eV) : 518.91 (M^+.).

¹H NMR (300 MHz, CDCl₃) : 7.65 (m, H_aromatic); 6.25 (t, J=6Hz, NH); 4.45 (d, J=6Hz, C1’-H2); 3.95 (m, C17-H); 0.74 (s, C28-H3) ; 1.03 (s, C29-H₃); 1.1 (d, J= 6Hz, C20-H₃); 0.85 (s, C19-H₃); 1.25 (d, J=6Hz, C18-H₃).

¹³C NMR (75 MHz, CDCl₃) : 65.22 (C1); 40.46 (C2); 32.75 (C3); 36.86 (C4); 43.74 (C5);30.44 (C6); 30.35 (C7); 43.79 (C8); 69.75 (C9); 40.63 (C10); 20.49 (C11); 48.74 (C12); 49.28 (C13); 32.751 (C14); 39.86 (C15); 175.287 (C16); 67.71 (C17); 28.35 (C18); 24.43 (C19); 20.49 (C20); 36.71 (C21); 23.24 (C22); 22.94 (C23); 21.06 (C24); 36.65 (C25); 21.56 (C26); 20.34 (C27); 15.17 (C28); 19.37 (C29); 44.20 (C1’); 138.87 (C2’); 128.06 (C2’); 128.92; (C3’) 128.06 (C4’); 127.59 (C5’).

References

1. Daoubi, M.; Benharref, A.; Kossareva, E.; Pierrot, M. Molecules. 2000, 5, M188.
2. Beugelmans, R.; Chastanet, J.; Ginsburg, H.; Quintero-Cortes, L.; Roussi, G. J. Org. Chem. 1985, 50, 4933-4938.

Sample Availability: Available from the authors and from MDPI.