A new method for the synthesis of the marine alkaloid fascaplysin

Tetrahedron Letters

Volumn 51, Issue 50, 2010, Pages 6498-6499

  Zhidkov, Maxim E ^a   Baranova, Olga V ^a   Kravchenko, Natalya S ^a   Dubovitskii, Sergey V ^a  

^a FAR EASTERN FEDERAL UNIVERSITY   (Russian Federation)

Author keywords

Fascaplysin; Homofascaplysin C; Pyrido 1 2 a:3 4 b diindole; Synthesis

Indexed keywords

ALKALOID; FASCAPLYSIN; HOMOFASCAPLYSIN C; INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BAEYER VILLIGER REACTION; DECARBOXYLATION; DRUG SYNTHESIS; METHODOLOGY; OXIDATION; STRUCTURE ACTIVITY RELATION;

EID: 78650252982     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.09.120     Document Type: Article

References (17)

1. Roll, D. M.; Ireland, C. M.; Lu, H. S.; Clardy, J.J. Org. Chem. 1988, 53, 3276-3278.
2. For example, see: (a) Jimenez, C.; Quinoa, E.; Adamczeski, M.; Hunter, L. M.; Crews, P.J. Org. Chem. 1991, 56, 3403-3410;
3. (b) Schmidt, E. W.; Faulkner, D. J. Tetrahedron Lett. 1996, 37, 3951-3954;
4. (c) Kirsch, G.; Konig, G. M.; Wright, A. D.; Kaminsky, R. ;. Nat. Prod. 2000, 63, 825-829;
5. (d) Charan, R. D.; McKee, T. C.; Gustafson, K. R.; Pannell, L. K.; Boyd, M. R. Tetrahedron Lett. 2002, 43, 5201-5204;
6. (e) Popov, A. M.; Stonik, V. A. Antibiot. Khimioter. 1991, 36, 12-14;
7. (f) Hormann, A.; Chaudhuri, B.; Fretz, H. Bioorg. Med. Chem. 2001, 9, 917-921.
8. Soni, R.; Muller, L.; Furet, P.; Schoepfer, J.; Stephan, C.; Zunstein-Mecker, S.; Fretz, H.; Chaudhuri, B. Biochem. Biophys. Res. Commun. 2000, 275, 877-884.
9. (a) Cribble, G. W.; Pelcman, B.J. Org. Chem. 1992, 57, 3636-3642;
10. (b) Rocca, P.; Marsais, F.; Godait, A; Quéguiner, G. Tetrahedron Lett. 1993, 34, 7917-7918;
11. (c) Molina, P.; Fresneda, M.; Garciazafra, S.; Almendros, P. Tetrahedron Lett. 1994, 35, 8851-8854;
12. (d) Radchenko, O. S.; Novikov, V. L.; Elyakov, G. B. Tetrahedron Lett. 1997, 38, 5339-5342.
13. Dubovitskii, S. V. Tetrahedron Lett. 1997, 37, 5207-5208.
14. Jirkovsky, L; Sontroch, G.; Bandy, R.; Oshiro, G.J. Med. Chem. 1987, 30, 388-394.
15. Bit, R. A.; Davis, P. D.; Hill, C. H.; Keech, E.; Vesey, D. R. Tetrahedron 1991, 47, 4645-4664.
16. 4a These conditions for Fischer rearrangement were first proposed in the publication: Murakami, Y.; Yokoyama, Y.; Miura, T.; Hirasawa, H.; Kamimura, Y.; Izaki, M. Heterocycies 1984, 22, 1211-1215.
17. 2O (3 × 10 mL) and acidified with hydrochloric acid. The combined aqueous layer was extracted with EtOAc (3×3 mL) and then evaporated under reduced pressure to give 2 as a red powder (52 mg, 67%); the main spectral characteristics of which were identical to those of fascaplysin.