A novel synthesis of (±)-harmacine and (±)1,2,3,4,6,7,12,12b- octahydroindole[2,3-a]quinolizine

Journal of Heterocyclic Chemistry

Volumn 44, Issue 6, 2007, Pages 1459-1463

  King, Frank D ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3,4,6,7,12,12B OCTAHYDROINDOLE[2,3 A]QUINOLIZINE; 5,5 DIETHOXYPENTAN 1 AMINE; AMINE; HARMACINE; QUINOLIZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 38949191385     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570440634     Document Type: Article

References (13)

1. King, F. D.; Brown, A. M.; Gaster, L. M.; Kaumann, A. J.; Medhurst, A. D.; Parker, S. G.; Parsons, A. A.; Patch, T. L.; Raval, P. J. Med. Chem., 1993, 36, 1918.
2. Poolsup, N.; Leelasangaluk, V.; Jittangtrong, J.; Rithlamlert, C.; Ratanapantamanee, N.; Khanthong, M. J. Clin. Pharm. Ther. 2005, 30, 521.
3. Knölker, H-J.; Agarwal, S. Synlett. 2004, 1767 and refs therein.
4. Hoefgen, B.; Decker, M.; Mohr, P.; Schramm, A.M.; Rostom, S.A.F.; El-Subbagh, H.; Schweikert, P.M.; Rudolf, D.R.; Kassack, M.U.; Lehmann, J. J. Med. Chem. 2006, 49, 760.
5. King, F. D. J. Chem. Soc. Perk. Trans. I, 1986, 447.
6. van Tamelen, E.E.; Weber, J.; Schiemenz, G.P.; Barker, W. Bioorganic Chem., 1976, 5, 283.
7. Ochiai, E,; Takahashi M. Chem. Pharm. Bull. 1965, 13, 618.
8. King, F. D. Tetrahedron Lett. 1983, 24, 3281.
9. The author thanks Rhodia Pharma Solutions Ltd. for the kind gift of 4-chlorobutyraldehyde diethyl acetal.
10. Fritz, H.; Pfaender, P. Chem. Ber., 1965, 98, 989.
11. Jackson, A.H.; Naidoo, B. Tetrahedron, 1969, 25, 4843.
12. Jackson, A.H.; Smith, P. Tetrahedron, 1968, 24, 2227.
13. Zhang, Y.; Hsung, R.P.; Zhang, X.; Huang, J.; Slafer, B.W.; Davis, A. Org Letts, 2005, 7, 1047.