First total synthesis of Louisianin A

Journal of Organic Chemistry

Volumn 71, Issue 16, 2006, Pages 6302-6304

  Chang, Ching Yao ^a   Liu, Hui Ming ^b   Chow, Tahsin J ^c  

^a ASIA UNIVERSITY   (Taiwan)

^b HUNGKUANG UNIVERSITY   (Taiwan)

^c INSTITUTE OF CHEMISTRY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIZATION- DECARBOXYLATION; CYCLOPENTENONE RING; LOUISIANIN;

ADDITION REACTIONS; CARBOXYLATION; CHLORINE COMPOUNDS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

2 CHLORO 4 CYANOPYRIDINE; 4 ALLYL 6,7 DIHDYRO 1 HYDROXYCYCLOPENTA[C]PYRIDIN 5 ONE; CYCLOPENTENONE; LOUISIANIN A; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DECARBOXYLATION; HYDROLYSIS; REACTION ANALYSIS; SYNTHESIS;

ALLYL COMPOUNDS; MOLECULAR STRUCTURE; PYRIDINES;

EID: 33746887073     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060935j     Document Type: Article

References (18)

1. Takamatsu, S.; Kim, Y.-P.; Hayashi, M.; Furuhata, K.; Takayanagi, H.; Komiyama, K.; Woodruff, H. B.; Omura, S. J. Antibiot. 1995, 48, 1090-1094.
2. Komiyama, K.; Takamatsu, S.; Kim, Y.-P.; Matsumoto, A.; Takahashi, Y.; Hayashi, M.; Woodruff, H. B.; Ômura, S. J. Antibiot. 1995, 48, 1086-1089.
3. Sunazuka, T.; Tian, Z.-M.; Harigaya, Y.; Takamatsu, S.; Hayashi, M.; Komiyama, K.; Ômura, S. J. Antibiot. 1997, 50, 274-275.
4. Beierle, J. M.; Osimboni, E. B.; Metallinos, C.; Zhao, Y.; Kelly, T. R. J. Org. Chem. 2003, 68, 4970-4972.
5. (a) Gribble, G. W.; Saulnier, M. G. Heterocycles 1993, 35, 151-169.
6. (b) Cochennec, C.; Rocca, P.; Marsais, F.; Godard, A.; Quéguiner, G. Synthesis 1995, 321-324 and references therein.
7. (c) Cailly, T.; Fabis, F.; Lemaître S.; Bouillon, A.; Rault, S. Tetrahedron Lett. 2005, 46, 135-137.
8. (a) Gribble, G. W.; Saulnier, M. G. Tetrahedron Lett. 1980, 21, 4137-4140.
9. (b) Karig, G.; Spencer, J. A.; Gallagher, T. Org. Lett. 2001, 3, 835-838.
10. (a) Trécourt, F.; Mallet, M.; Mongin, O.; Quéguiner, G. J. Org. Chem. 1994, 59, 6173-6178.
11. (b) Ohtsu, H.; Itokawa, H.; Xiao, Z.; Su, C.-Y.; Shin, C. C.-Y.; Chiang, T.; Chang, E.; Lee, Y.; Chiu, S.-Y.; Chang, C.; Lee, K.-H. Bioorg. Med. Chem. 2003, 11, 5083-5090.
12. (a) Plisson, C.; Chenault, J. Heterocycles 1999, 51, 2627-2638.
13. (b) Vallin, K. S. A.; Emilsson, P.; Larhed, M.; Hallberg, A. J. Org. Chem. 2002, 67, 6243-6246.
14. (c) de Vries, A. H. M.; Mulders, J. M. C. A.; Mommers, J. H. M.; Henderickx, H. J. W.; de Vries, J. G. Org. Lett. 2003, 5, 3285-3288.
15. (d) Yasuda, N.; Hsiao, Y.; Jensen, M. S.; Rivera, N. R.; Yang, C.; Wells, K. M.; Yau, J.; Palucki, M.; Tan, L.; Dormer, P. G.; Volante, R. P.; Hughes, D. L.; Reider, P. J. J. Org. Chem. 2004, 69, 1959-1966.
16. Windscheif, P.-M.; Vögtle, F. Synthesis 1994, 87-92.
17. (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524.
18. (b) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478-5486.