Asymmetric Total Synthesis of (-)-Leuconoxine via Chiral Phosphoric Acid Catalyzed Desymmetrization of a Prochiral Diester

Organic Letters

Volumn 17, Issue 1, 2015, Pages 154-157

  Higuchi, Kazuhiro ^a   Suzuki, Shin ^a   Ueda, Reeko ^a   Oshima, Norifumi ^a   Kobayashi, Emiko ^a   Tayu, Masanori ^a   Kawasaki, Tomomi ^a  

^a MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDONE DERIVATIVE; INDOLE ALKALOID; LACTAM; LEUCONOXINE; PHOSPHORIC ACID;

APOCYNACEAE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

APOCYNACEAE; CATALYSIS; CYCLIZATION; INDOLE ALKALOIDS; LACTAMS; MOLECULAR STRUCTURE; PHOSPHORIC ACIDS; PYRROLIDINONES; STEREOISOMERISM;

EID: 84925235352     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol5033865     Document Type: Article

References (32)

1. Verpoorte, R.; van der Heijden, R.; Moreno, P. R. H. In The Alkaloids: Chemistry and Pharmacology; Cordell, G. A., Ed.; Academic Press: San Diego, 1997; Vol. 49, p 221.
2. Takayama, H.; Sakai, S.-I. In The Alkaloids: Chemistry and Biology; Cordell, G. A., Ed.; Academic Press: New York, 1998; Vol. 50, p 415.
3. Kam, T.-S.; Lim, K.-H. In The Alkaloids: Chemistry and Biology; Cordell, G. A., Ed.; Academic Press: The Netherlands, 2008; Vol. 66, p 1.
4. Abe, F.; Yamauchi, T. Phytochemistry 1994, 35, 169
5. Higuchi, K.; Sato, Y.; Tsuchimochi, M.; Sugiura, K.; Hatori, M.; Kawasaki, T. Org. Lett. 2009, 11, 197
6. Higuchi, K.; Sato, Y.; Kojima, S.; Tsuchimochi, M.; Sugiura, K.; Hatori, M.; Kawasaki, T. Tetrahedron 2010, 66, 1236
7. Hiemstra, H.; Sno, M. H. A. M.; Vijn, R. J.; Speckamp, W. N. J. Org. Chem. 1985, 50, 4014
8. Raheem, I. T.; Thiara, P. S.; Jacobsen, E. N. Org. Lett. 2008, 10, 1577
9. Muratore, M. E.; Holloway, C. A.; Pilling, A. W.; Storer, R. I.; Trevitt, G.; Dixon, D. J. J. Am. Chem. Soc. 2009, 131, 10796
10. Ascic, E.; Jensen, J. F.; Nielsen, T. E. Angew. Chem., Int. Ed. 2011, 50, 5188
11. Akiyama, T. Chem. Rev. 2007, 107, 5744
12. Kampen, D.; Reisinger, C. M.; List, B. Top. Curr. Chem. 2010, 291, 395
13. Terada, M. Synthesis 2010, 1929
14. Rueping, M.; Kuenkel, A.; Atodiresei, I. Chem. Soc. Rev. 2011, 40, 4539
15. Wakchaure, V. N.; List, B. Angew. Chem., Int. Ed. 2010, 49, 4136
16. Gualtierotti, J.-B.; Pasche, D.; Wang, Q.; Zhu, J. Angew. Chem., Int. Ed. 2014, 53, 9926
17. Wilent, J.; Petersen, K. S. J. Org. Chem. 2014, 79, 2303
18. López-García, M.; Alfonso, I.; Gotor, V. Tetrahedron: Asymmetry 2003, 14, 603
19. Xu, Z.; Wang, Q.; Zhu, J. J. Am. Chem. Soc. 2013, 135, 19127
20. Umehara, A.; Ueda, H.; Tokuyama, H. Org. Lett. 2014, 16, 2526
21. Yang, Y.; Bai, Y.; Sun, S.; Dai, M. Org. Lett. 2014, 16, 6216
22. Gudjons, J.; Oehl, R.; Rosenmund, P. Chem. Ber. 1976, 109, 3282
23. Taga, M.; Ohtsuka, H.; Inoue, I.; Kawaguchi, T.; Nomura, S.; Yamada, K.; Date, T.; Hiramatsu, H.; Sato, Y. Heterocycles 1996, 42, 251
24. Martin, C. L.; Overman, L. E.; Rohde, J. M. J. Am. Chem. Soc. 2008, 130, 7568
25. Bao, J.; Wulff, W. D.; Dominy, J. B.; Fumo, M. J.; Grant, E. B.; Rob, A. C.; Whitcomb, M. C.; Yeung, S.-M.; Ostrander, R. L.; Rheingold, A. L. J. Am. Chem. Soc. 1996, 118, 3392
26. Magolan, J.; Carson, C. A.; Kerr, M. A. Org. Lett. 2008, 10, 1437
27. Marra, A.; Moni, L.; Pazzi, D.; Corallini, A.; Bridi, D.; Dondoni, A. Org. Biomol. Chem. 2008, 6, 1396
28. DeLorbe, J. E.; Jabri, S. Y.; Mennen, S. M.; Overman, L. E.; Zhang, F.-L. J. Am. Chem. Soc. 2011, 133, 6549
29. Bestmann, H. J.; Schmid, G.; Sandmeier, D. Angew. Chem., Int. Ed. Engl. 1976, 15, 115
30. Bestmann, H. J. Angew. Chem., Int. Ed. Engl. 1977, 16, 349
31. Schobert, R.; Boeckman, R. K., Jr.; Pero, J. E. Org. Synth. 2005, 82, 140
32. Feng, T.; Cai, X.-H.; Liu, Y.-P.; Li, Y.; Wang, Y.-Y.; Luo, X.-D. J. Nat. Prod. 2010, 73, 22