The Malaysian Journal of Analytical Sciences Vol 16 No 1 (2012): 43 – 48

 

 

 

SYNTHESIS OF LACTONE LACTAM : A USEFUL PRECURSOR TOWARDS (-)-GEISSMAN WAISS LACTONE

 

(Sintesis Lakton Laktam : Prekursor yang penting untuk sintesis (-)-Geissman Waiss Lakton)

 

Mohd Tajudin Mohd Ali^1,2* and Oliver Reiser¹

 

¹Institut fur Organische Chemie,

Universität Regesnburg, Universitätsstr. 31, 93053 Regensburg, Germany

²Faculty of Applied Sciences,

Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia.

 

*Corresponding author: tajudinali@salam.uitm.edu.my

 

 

Abstract

Retronecine is found widely in numerous alkaloids such as senecionine, seneciphylline and retrorsine. It belongs to the pyrrolizidine type alkaloids, which are also found in many plants. Extracts of plants containing these alkaloids have been used in traditional herbal medicine.¹ Many of these alkaloids show interesting biological activities including hepatotoxic, antitumor, hypotensive, anti-inflammatory and antispasmolytic activities.² (-)-Lactone lactam could be serve as a valuable starting material towards the synthesis of retronecine through (-) Geissman Waiss lactone³. The synthesis of (-)-lactone lactam   was performed starting from benzene in 6 steps.

 

Keywords: retronecine, Geissman Weiss lactone, (-)-lactone lactam, γ -butyrolactone

 

References

1.       Mattocks, A.R. Chemistry and Toxicology of pyrrolizidine Alkaloids ; Academic : London 1986.

2.       Geissman, T. A.; Waiss, A.C. J. Org. Chem. 1962, 27, 139-142.

3.       Haruki, N.; Osamu, O.; Yasuyoshi, M.; Youichi, U.; Kiyoyuki, Y. J. Org. Chem. 1987, 52, 2941-2943.

4.       (a) Jeremy, C.; Peter, G.; David, W. K. Chem. Comm. 1988, 8, 509-510. 

(b) Jeremy, C.; Peter, G.; David, W. K. J. Chem.  Soc. Perkin Trans. 1 1993, 1313-1317.

5.     Andrew, G. H. W. J. Org. Chem. 2001, 66, 8513-8517.

6.     (a)  Antonio, R. F.; Carlos, R. R. M.; Carlos. R.D.C. Tetrahedron Letters. 1993, 34, 27-30.

        (b) Paulo, C. M. L. M.; Carlos,   R D. D. C. Tetrahedron Letters. 1999, 40, 7735-7738.

7.     Patrick, J.; Bertrand, C. J. Chem. Soc. Perkin Trans. 1. 1987, 1177-1182.

8.     Luis, E. M.; James, L. L.; Douglas, H. C.; Eric, N. J. J. Am. Chem. Soc. 1995,  117, 5897-5898.9

9.     H. Kotsuki, T. Ohishi, T. Araki. Tetrahedron Letters, 1997, 38(12), 2129-2132