Molecules 2001, 6, M228

Molecules 2001, 6, M228

(1S,2S,3R,6R,7R)-Epoxy-himachal-7-ol

M. Dakir, E. Lassaba, A. Chekroun and A. Benharref

Laboratoire de Chimie des Substances Naturelles et des Hétérocycles, Département de Chimie, Faculté des Sciences-SemLalia, B.P. 2390, 40001 Marrakech, Maroc. E-mail: [email protected]

Received: 12 February 2001 / Accepted: 15 May 2001 / Published: 25 May 2001

To a mixture of lithium aluminium hydride (0,16 g, 4 mmol) in dry ether (50 mL) [1] was added a solution of (10 mL) of epoxide 1 [1,2] (1 g, 4 mmol) in dry ether dropwise at room temperature. After stirring for 24 hours, the mixture is hydrolysed with 5 mL of water, filtered and extracted with ether. The combined extracts were dried with Na₂SO₄, concentrated and purified by chromatography on silica gel column using hexane/chloroform: 8/2 as solvent to give 2 (100 %).

MS (EI, 70eV): 238 (M^+.).

¹H NMR (400 MHz, CCl₄): 0.88 (s,C14-H₃), 1.05(s,C15-H₃); 1.15 (s, C12-H₃); 1.32 (s, C13-H₃); 2.97 (s,C2-H).

¹³C NMR (100 MHz, CCl₄): 46.25 (C1), 63.91 (C2), 56.94 (C3), 38.75 (C4), 35 (C5), 45 (C6), 73.38 (C7), 40 (C8), 35.1 (C9),30 (C10), 41.25 (C11), 25 (C12), 31.25 (C13), 22.5 (C14), 21.25 (C15).

References

1. Kiyomi, K.; Ippei, N.; Fumiyuki, M.; Morio, N.; Mikihiro, O.; Yochito, T.; Hideo, K. J. Org. Chem. 1995, 60, 3318-3333.
2. Lassaba, E.; Eljamili, H.; Chekroun, A.; Benharref, A.; Chiarooni, A.; Riche C.; Lavergne, J.-P. Syn Comm. 1998, 28, 2641-2651.
3. Chiaroni, A.; Riche, C.; Benharref, A.; Chekroun, A.; Lavergne, J.-P. Acta Cryst. 1992, C48, 1720.

Sample Availability: Available from the authors and from MDPI.