Total synthesis of polyamine toxin HO-416b utilizing the 2- nitrobenzenesulfonamide protecting group

Tetrahedron Letters

Volumn 40, Issue 25, 1999, Pages 4711-4714

  Hidai, Yuko ^a   Kan, Toshiyuki ^a   Fukuyama, Tohru ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

2 nitrobenzenesulfonamide (Ns); HO 416b; Polyamine toxin; Solid support

Indexed keywords

GLUTAMATE RECEPTOR ANTAGONIST; HO 416B; HO 461B; NITROBENZENE DERIVATIVE; POLYAMINE; SPIDER VENOM; SULFONAMIDE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

ARANEAE;

EID: 0033580953     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00851-5     Document Type: Article

References (13)

1. 1. For a review of the pharmacology of polyamine toxins from spiders and wasps, see: Mueller, A. L.; Roeloffs, R.; Jackson, H. The Alkaloids 1995, 46, Chapter 2.
2. 2. For a review of polyamine toxins from spiders and wasps, see: (a) Schafer, A.; Benz, H.; Fiedler, W.; Guggisberg, A.; Bienz, S.; Hesse, M. The Alkaloids 1994, 45, Chapter 1.
3. (b) Miyashita, M. J. Syn. Chem. Org. Jpn. 1996, 54, 846.
4. 3. (a) Fukuyama, T.; Jow, C.-K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373.
5. (b) Fukuyama, T.; Cheung, M.; Jow, C.-K.; Hidai, Y.; Kan; T. Tetrahedron Lett. 1997, 38, 5831.
6. 4. Quistad, G. B.; Reuter, C. C; Skinner, W. S.; Dennis, P. A.; Suwanrumpha, S.; Fu, E. W. Toxicon. 1991, 29, 329.
7. 5. Fiedler, W. J.; Hesse, M. Helv. Chim. Acta 1993, 76, 1511.
8. 2O) gave 2 (38.0 g, 58.8 %) as a yellow powder.
9. 7. Burton, H.; Cheeseman, G. W. H. J. Chem. Soc. 1955, 887, 3089.
10. 8. The Merrifield resins (2 % DVB, 100-200 mesh) were purchased from Novabiocheme.
11. 2 at room temperature under an argon atmosphere. After stirring for 30min, the solvent was evaporated and the residue dried in vacuo to provide 1.54 g of the resin 14.
12. 10. Although Ns group can be deprotected by treatment with a variety of thiolates, we used the conditions already tested for a solid-state synthesis. Miller, S. C.; Scanlan, T. S. J. Am. Chem. Soc. 1997, 119, 2301
13. 2 (1 : 9).