Synthesis of huperzine B through ring closing metathesis

Tetrahedron Letters

Volumn 45, Issue 2, 2004, Pages 285-287

  Choi Lee, Ihl Young ^a   Hong, Joong Yeoun ^a   Jung, Myung Hee ^a   Lee, Hyo Won ^b  

^a Korea Research Institute of Chemical Technology   (South Korea)

^b Chungbuk National University   (South Korea)

Author keywords

Acetylcholinesterase (AChE) inhibitor; Huperzine; Ring closing metathesis

Indexed keywords

ALKENYL GROUP; AMINE; HUPERZINE B;

ARTICLE; CHEMICAL REACTION; CURTIUS REARRANGEMENT; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROGENATION; HYDROLYSIS; ISOMERIZATION; REACTION ANALYSIS; RING CLOSING METATHESIS;

EID: 0347627371     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.10.169     Document Type: Article

References (13)

1. Liu J.-S., Zhu Y.-L., Yu C.-M., Zhou Y.-Z., Han Y.-Y., Wu F.-W., Qi B.-F. Can. J. Chem. 64:1986;837-839.
2. (a) Tang X.-C., Sarno P., Sugaya K., Giacobini E. J. Neurosci. Res. 24:1989;276-285
3. (b) Kozikowski A.P. J. Heterocyclic Chem. 27:1999;97-105
4. (c) Bai D. Pure Appl. Chem. 65:1993;1103-1112.
5. Yan X.F., Lu W.H., Lou W.J. Acta Pharmacol. Sin. 8:1987;117.
6. Wu B., Bai D. J. Org. Chem. 62:1997;5978-5981
7. (b) Rajendran V., Rong S.-B., Saxena A., Doctor B.P., Kozikowski A.P. Tetrahedron Lett. 42:2001;5359-5361
8. (c) Rajendran V., Saxena A., Doctor B.P., Kozikowski A.P. Bioorg. Med. Chem. Lett. 12:2002;1521-1523
9. (d) Abstract of Taber, D. F. from 35th ACS Middle Atlantic Regional Meeting.
10. (a) Kozikowski A.P., Xia Y., Reddy E.R., Tuckmantel W., Hanin I., Tang X.C. J. Org. Chem. 56:1991;4636-4645
11. (b) Campiani G., Sun L.-Q., Kozikowski A.P., Aagaard P., McKinney M. J. Org. Chem. 58:1993;7660-7669.
12. Briot A., Bujard M., Gouverneur V., Nolan S.P., Mioskowski C. Org. Lett. 2:2000;1517-1519.
13. 3) δ 162.6, 153.3, 140.2, 135.9, 133.1, 132.3, 125.2, 115.8, 108.5, 53.9, 53.3, 47.9, 41.7, 40.3, 39.6, 26.4, 22.8; MS ( m/z , rel int): 268 (100), 253 (92), 211, 154, 43.