A short synthesis of (+)-lycoricidine

Tetrahedron

Volumn 58, Issue 36, 2002, Pages 7335-7338

  Elango, Shanmugham ^a   Yan, Tu Hsin ^a  

^a NATIONAL CHUNG HSING UNIVERSITY   (Taiwan)

Author keywords

Bromohydrin; Cycloaddition

Indexed keywords

ALKALOID DERIVATIVE; EPOXIDE; LYCORICIDINE; POLYCYCLIC AROMATIC HYDROCARBON; TIN CHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; CYCLOADDITION; PRIORITY JOURNAL; SYNTHESIS;

ARENE;

EID: 0037008919     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00736-6     Document Type: Article

References (15)

1. (a) Pettit, G.R.; Gaddamidi, V.; Cragg, G.M.; Herald, D.L.; Sawaga Y. J. Chem. Soc., Chem. Commun. 1984, 1693.
2. (b) Pettit G.R., Gaddamidi V., Herald D.L., Singh S.B., Cragg G.M., Schmidt J.M., Boettner F.E., Williams M., Sawaga Y. J. Nat. Prod. 49:1986;995.
3. (a) Hudlicky T., Olivo H.F. J. Am. Chem. Soc. 114:1992;9694.
4. (b) Hudlicky T., Olivo H.F., McKibben B. J. Am. Chem. Soc. 116:1994;5108.
5. (c) Chida N., Ohtsuka M., Ogawa S. J. Org. Chem. 58:1993;4441.
6. (d) McIntosh M.C., Weinreb S.M. J. Org. Chem. 58:1993;4823.
7. For some other syntheses of (+)-lycoricidine, see: (a) Keck G.E., Wager T.T., Rodriquez J.F.D. J. Am. Chem. Soc. 121:1999;5176 (b) Chida N., Ohtsuka M., Ogawa S. Tetrahedron Lett. 32:1991;4525 (c) Paulsen H., Stubbe M. Tetrahedron Lett. 23:1982;3171 Paulsen H., Stubbe M. Liebigs Ann. Chem. 1983;535.
8. For some other syntheses of (+)-lycoricidine, see: (a) Keck G.E., Wager T.T., Rodriquez J.F.D. J. Am. Chem. Soc. 121:1999;5176 (b) Chida N., Ohtsuka M., Ogawa S. Tetrahedron Lett. 32:1991;4525 (c) Paulsen H., Stubbe M. Tetrahedron Lett. 23:1982;3171 Paulsen H., Stubbe M. Liebigs Ann. Chem. 1983;535.
9. For some other syntheses of (+)-lycoricidine, see: (a) Keck G.E., Wager T.T., Rodriquez J.F.D. J. Am. Chem. Soc. 121:1999;5176 (b) Chida N., Ohtsuka M., Ogawa S. Tetrahedron Lett. 32:1991;4525 (c) Paulsen H., Stubbe M. Tetrahedron Lett. 23:1982;3171 Paulsen H., Stubbe M. Liebigs Ann. Chem. 1983;535.
10. For some other syntheses of (+)-lycoricidine, see: (a) Keck G.E., Wager T.T., Rodriquez J.F.D. J. Am. Chem. Soc. 121:1999;5176 (b) Chida N., Ohtsuka M., Ogawa S. Tetrahedron Lett. 32:1991;4525 (c) Paulsen H., Stubbe M. Tetrahedron Lett. 23:1982;3171 Paulsen H., Stubbe M. Liebigs Ann. Chem. 1983;535.
11. For precursors 5 and 9, see: Elango S., Wang Y.-C., Cheng C.-L., Yan T.-H. Tetrahedron Lett. 43:2002;3757.
12. The more hindered epoxide can usually be prepared by bromohydrin formation and base-promoted closure, see: Hanselaer R., Samson R., Vandewalle M. Tetrahedron. 34:1978;2393.
13. 2AlCl-assisted cyclization of 12, which in turn was derived from the base-assisted aza-Payne rearrangement of tosylaziridine: Rinner U., Siengalewicz P., Hudlicky T. Org. Lett. 4:2002;115.
14. Hamada T., Nishida A., Yonemitsu O. J. Am. Chem. Soc. 108:1986;140.
15. Elango, S.; Yan, T.-H. Submitted for publication.