The alkyne pathway to keramadine from the marine sponge Agelas sp.

Tetrahedron Letters

Volumn 39, Issue 17, 1998, Pages 2541-2544

  Lindel, Thomas ^a   Hochgürtel, Matthias ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Alkaloids; Aminoimidazoles; Marine natural products; Total synthesis

Indexed keywords

ALKALOID DERIVATIVE; IMIDAZOLE DERIVATIVE; KERAMADINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLIZATION; DIMERIZATION; HYDROGENATION; METHYLATION; REACTION ANALYSIS; SPONGE (PORIFERA); SYNTHESIS;

AGELAS; PORIFERA;

EID: 0032560064     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00341-4     Document Type: Article

References (17)

1. [1] (a) Garcia, EE; Benjamin, LE; Fryer, RI. J. Chem. Soc., Chem. Commun. 1973:78-79. The term "oroidin alkaloids" is used by
2. (b) Jiménez, C; Crews, P. Tetrahedron Lett, 1994;35:1375-1378.
3. [2] For a recent summary on the oroidin alkaloids see: Gribble, GW. Fortschr. Chem. Org. Naturst., Vol. 68; Herz, W; Kirby, GW; Moore, RE; Steglich, W; Tamm, C, editors.; Wien; Springer: Wien, 1996:137ff.
4. [3] Nakamura, H; Ohizumi, Y; Kobayashi, J; Hirata, Y. Tetrahedron Lett. 1984;25:2475-2478.
5. [4] (a) D'Ambrosio, M; Guemero, A; Chiasera, G; Pietra, F. Helv. Chim. Acta 1994;77:1895-1902. For a biomimetic cyclization of a non-cyclized oroidin alkaloid, see:
6. (b) Foley, LH; Büchi, G. J. Am. Chem. Soc. 1982;104:1776-1777.
7. [5] The only known, recent synthesis of keramadine (1) employs a Wittig-Schweizer reaction to generate the (Z)-double bond: Daninos-Zeghal, S; Al Mourabit, A; Ahond, A; Poupat, C; Potier, P. Tetrahedron 1997;53:7605-7614.
8. [6] Braun, M; Büchi, G. J. Am. Chem. Soc. 1976;98:3049-3050.
9. [7] Cliff, MD; Pyne, SG. J. Org. Chem. 1995:60:2378-2383.
10. [8] Bailey, DM; Johnson, RE. J. Med. Chem. 1973;16:1300-1302.
11. [9] Sonogashira, K; Tohda, Y; Hagihara, N. Tetrahedron Lett. 1975; 16:4467-4470.
12. [10] Narasimham, NS; Ammanamanchi, R. Tetrahedron Lett. 1983;23:4733-4734.
13. 79Br): calcd. 323.0382; found 323.0383.
14. [12] For the use of radiolabelled amino acids in biosynthetic studies with marine sponges, see: (a) Lill, RE; Major, DA; Blunt, JW; Munro, MHG; Battershill, CN; McLean, MG; Baxter, RL. J. Nat. Prod. 1995;58:306-311.
15. (b) Carney, JR; Rinehart, KL. ibid. 1995;58:971-985.
16. (c) Garson, MJ. Nat. Prod. Rep. 1989:6:144-170. Feeding of tritiated steroid precursors to marine sponges:
17. (d) Rabinowitz, MH; Djerassi, C. J. Am. Chem. Soc. 1992;114:304-317.