Erratum: Synthetic studies on (+)-Manzamine A: Stereoselective synthesis of the tetracyclic core framework (Org. Lett. (2008) 10: 15 (3251-3253) DOI: 10.1021/ol801111r);Synthetic studies on (+)-manzamine A: Stereoselective synthesis of the tetracyclic core framework

Organic Letters

Volumn 10, Issue 15, 2008, Pages 3251-3253

  Kita, Yoichi ^a   Toma, Tatsuya ^a   Kan, Toshiyuki ^b   Fukuyama, Tohru ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAZOLE DERIVATIVE; MANZAMINE A; POLYCYCLIC HYDROCARBON;

ARTICLE; STEREOISOMERISM; SYNTHESIS;

CARBAZOLES; POLYCYCLIC COMPOUNDS; STEREOISOMERISM;

EID: 49649093606     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol500161f     Document Type: Erratum

References (33)

1. (a) Sakai, R.; Higa, T.; Jefford, C. W.; Bernardinelli, G. J. Am. Chem. Soc. 1986, 108, 6404.
2. Nakamura, H.; Deng, S.; Kobayashi, J.; Ohizumi, Y.; Tomotake, Y.; Matsuzaki, T.; Hirata, Y. Tetrahedron Lett. 1987, 28, 621.
3. (a) Ang, K. K. H.; Holmes, M. J.; Higa, T.; Hamann, M. T.; Kara, U. A. K. Antimicrob. Agents Chemother. 2000, 44, 1645.
4. (b) El Sayed, K. A.; Kelly, M.; Kara, U. A. K.; Ang, K. K. H.; Katsuyama, I.; Dunbar, D. C.; Khan, A. A.; Hamann, M. T. J. Am. Chem. Soc. 2001, 123, 1804.
5. (c) Winkler, J. D.; Londregan, A. T.; Hamann, A. T. Org. Lett. 2006, 8, 2591.
6. (d) Winkler, J. D.; Londregan, A. T.; Ragains, J. R.; Hamann, A. T. Org. Lett. 2006, 8, 3407.
7. (e) Winkler, J. D.; Londregan, A. T.; Hamann, A. T. Org. Lett. 2007, 9, 4467.
8. Edrada, R. A.; Proksch, P.; Wray, V.; Witte, L.; Müller, W. E. G.; Van Soest, R. W. M. J. Nat. Prod. 1996, 59, 1056.
9. Mayer, A. M. S.; Gunasekara, S. P.; Pomponi, S. A.; Sennet, S. H. PCT Int. Appl., WO 0056304 A2 20000928, 2000.
10. Rao, K. V.; Donia, M. S.; Peng, J.; Garcia-Palomero, E.; Alonso, D.; Martinez, A.; Medina, M.; Franzblau, S. G.; Tekwani, B. L.; Khan, S. I.; Wahyuono, S.; Willett, K. L.; Hamann, M. T. J. Nat. Prod. 2006, 69, 1034.
11. For reviews of manzamine alkaloid, see: (a) Tsuda, M.; Kobayashi, J. Heterocycles 1997, 46, 725.
12. (b) Magnier, E.; Langlois, Y. Tetrahedron 1998, 54, 6201.
13. (a) Winkler, J. D.; Axten, J. M. J. Am. Chem. Soc. 1998, 120, 6425.
14. (b) Martin, S. F.; Humphrey, J. M.; Ali, A.; Hillier, M. C J. Am. Chem. Soc. 1999, 121, 866.
15. (c) Humphrey, J.; Liao, Y.; Ali, A.; Rein, T.; Wong, Y.-L.; Chen, H.-J.; Courtney, A. K.; Martin, S. F. J. Am. Chem. Soc. 2002, 124, 8584.
16. (d) Tokumaru, K.; Arai; S., ; Nishida, A. 126th Annual Meeting of the Pharmaceutical Society of Japan, Sendai, 2006; 028[F]-031.
17. (a) Kondo, K.; Shigemori, H.; Kikuchi, Y.; Ishibashi, M.; Sasaki, T.; Kobayashi, J. J. Org. Chem. 1992, 57, 2480.
18. (b) Choo, Y.-M.; Hamann, M. T Heterocycles 2007, 71, 245.
19. For a review on Ns chemistry, see: (a) Kan, T.; Fukuyama, T. J. Syn. Org. Chem., Jpn. 2001, 59, 779.
20. (b) Kan, T.; Fukuyama, T. Chem. Commun. 2004, 1204.
21. (a) Fukuyama, T.; Jow, C.-K.; Hidai, Y.; Kan, T. Tetrahedron Lett. 1995, 36, 6373.
22. (b) Fukuyama, T.; Cheung, M.; Jow, C.-K.; Hidai, Y.; Kan, T. Tetrahedron Lett. 1997, 38, 5831.
23. (c) Fukuyama, T.; Cheung, M.; Kan, T. Synlett 1999, 1301.
24. (d) Kurosawa,W.; Kan, T.; Fukuyama, T. Org. Synth. 2002, 79, 186.
25. Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125.
26. Schmidt, U; Lieberknecht, A; Wild, J. Synthesis 1984, 53.
27. For construction of 8-membered ring by Ns-strategy, see: (a) Kan, T.; Kobayashi, H.; Fukuyama, T. Synlett 2002, 697.
28. Similar deprotection of Ms group by LDA, see: (a) Ritter, T.; Stanek, K.; Larrosa, I.; Carreira, E. M. Org. Lett. 2004, 6, 1513.
29. For a review, see: Zimmer, H.; Lankin, D. C.; Horgan, S. W Chem. Rev. 1971, 71, 229.
30. Janey, J. M.; Iwama, T.; Kozmin, S. A.; Rawal, V. H. J. Org. Chem. 2000, 65, 9059.
31. (a) Cho, S. H.; Yoo, E. J.; Bae, I.; Chang, S. J. Am. Chem. Soc. 2005, 127, 16046.
32. (b) Cho, S. H.; Chang, S. Angew. Chem., Int. Ed. 2007, 46, 1897.
33. Utilizing other phosphines or employing typical Mitsunobu conditions did not provide the desired product.