A new total synthesis of porritoxin

Journal of Organic Chemistry

Volumn 71, Issue 8, 2006, Pages 3303-3305

  Moreau, Anne ^a   Lorion, Magali ^a   Couture, Axel ^a   Deniau, Eric ^a   Grandclaudon, Pierre ^a  

^a UNIV LILLE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYAKYL CHAIN; PARHAM CYCLIZATION METHODOLOGY; PHYTOTOXIN PORRITOXIN;

NITROGEN COMPOUNDS; SYNTHESIS (CHEMICAL);

BIOCHEMISTRY;

ALKALOID; ISOINDOLE DERIVATIVE; PLANT TOXIN; PORRITOXIN; UNCLASSIFIED DRUG;

ARTICLE; COMPLEX FORMATION; CYCLIZATION; PRODUCTIVITY; REACTION ANALYSIS; STRUCTURE ANALYSIS; TOXIN SYNTHESIS;

INDOLES; ISOINDOLES; MOLECULAR STRUCTURE;

EID: 33645771136     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052592f     Document Type: Article

References (24)

1. Suemitsu, R.; Ohnishi, K.; Horiuchi, M.; Kitaguchi, A.; Odamura, K. Phytochemistry 1992, 31, 2325-2326.
2. Horiuchi, M.; Maoka, T.; Iwase, N.; Ohnishi, K. J. Nat. Prod. 2002, 65, 1204-1205.
3. Cornella, I.; Kelly, T. R. J. Org. Chem. 2004, 69, 2191-2193.
4. (a) Hoarau, C.; Couture, A.; Cornet, H.; Deniau, E.; Grandclaudon, P. J. Org. Chem. 2001, 66, 8064-8069.
5. (b) Couture, A.; Deniau, E.; Grandclaudon, P.; Hoarau, C.; Rys, V. Tetrahedron Lett. 2002, 43, 2207-2210.
6. (c) Moreau, A.; Couture, A.; Deniau, E.; Grandclaudon, P.; Lebrun, S. Tetrahedron 2004, 60, 6169-6176.
7. (d) Moreau, A.; Couture, A.; Deniau, E.; Grandclaudon, P. J. Org. Chem. 2004, 69, 4527-4530.
8. (e) Rys, V.; Couture, A.; Deniau, E.; Lebrunj S.; Grandclaudon, P. Synlett 2004, 2233-2235.
9. (f) Moreau, A.; Couture, A.; Deniau, E.; Grandclaudon, P. Eur. J. Org. Chem. 2005, 3437-3442.
10. (g) Deniau, E.; Enders, D.; Couture, A.; Grandclaudon, P. Tetrahedron: Asymmetry 2005, 16, 875-881.
11. Reviews: (a) Parham, W. E.; Bradsher, C. K. Acc. Chem. Res. 1982, 15, 300-305.
12. (b) Wakefield, B. J. The Chemistry of Organolithium Compounds, 2nd ed.; Pergamon: New York, 1990.
13. (c) Gray, M.; Tinkl, M.; Snieckus, V. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Exeter, 1995; Vol. 11, pp 66-92.
14. (d) Ardeo, A.; Collado, M. I.; Osante, I.; Ruiz, J.; Sotomayor, N.; Lete, E. In Targets in Heterocyclic Systems; Atanassi O., Spinelli, D., Eds.; Italian Society of Chemistry: Rome, 2001; Vol. 5, pp 393-418.
15. (e) Clayden, J. Organolithiums: Selectivity for Synthesis; Elsevier Science Ltd.: Oxford, 2002.
16. (f) Mealy, M. J.; Bailey, W. F. J. Organomet. Chem. 2002, 646, 59-67.
17. (g) Sotomayor, N.; Lete, E. Curr. Org. Chem., 2003, 7, 275-300.
18. (h) Nájera, C.; Sansano, J. M.; Yus, M. Tetrahedron 2003, 59, 9255-9303.
19. (a) Carmen de la Fuente, M.; Dominguez, D. Tetrahedron 2004, 60, 10019-10028.
20. (b) Giger, R. K. A. Swiss Pat. 1985, CH 648300; Chem. Abstr. 1985, 103, 71188.
21. (c) Rys, V.; Couture, A.; Deniau, E.; Grandclaudon, P. Eur. J. Org. Chem. 2003, 1231-1237.
22. Moreau, A.; Couture, A.; Deniau, E.; Grandclaudon, P.; Lebrun, S. Org. Biomol. Chem. 2005, 3, 2305-2309.
23. (a) van Oijen, A. H.; Huck, N. P. M.; Kruijtzer, J. A. W.; Erkelens, C.; van Boom, J. H.; Liskamp, R. M. J. J. Org. Chem. 1994, 59, 2399-2408.
24. (b) Vieira, E.; Bingelli, A.; Breu, V.; Bur, D.; Fischli, W.; Güller, R.; Hirth, G.; Märki, H. P.; Müller, M.; Oefner, C.; Scalone, M.; Stadler, H.; Wilhelm, M.; Wostl, W. Bioorg. Med. Chem. Lett. 1999, 9, 1397-1402.