Enantioselective total synthesis of (+)-gliocladin C

Organic Letters

Volumn 9, Issue 2, 2007, Pages 339-341

  Overman, Larry E ^a   Shin, Youseung ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDONE DERIVATIVE; ALKALOID; BIOLOGICAL PRODUCT; GLIOCLADIN C; PIPERAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS;

ALKALOIDS; BIOLOGICAL PRODUCTS; MOLECULAR CONFORMATION; PIPERAZINES; PYRROLIDINONES; STEREOISOMERISM;

EID: 33846599334     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062801y     Document Type: Article

References (33)

1. Blunt, J. W.; Copp, B. R.; Munro, M. H. G.; Northcote, P. T.; Prinsep, M. R. Nat. Prod. Rep. 2006, 23, 26-78 and earlier reviews in this series.
2. Usami, Y.; Yamaguchi, J.; Numata, A. Heterocycles 2004, 63, 1123-1129.
3. Takahashi, C.; Numata, A.; Ito, Y.; Matsumura, E.; Araki, H.; Iwaki, H.; Kushida, K. J. Chem. Soc., Perkin Trans. 1 1994, 1859-1864.
4. Dong, J.-Y.; He, H.-P.; Shen, Y.-M; Zhang, K.-Q. J. Nat. Prod. 2005, 68, 1510-1513.
5. Feng, Y.; Blunt, J. W.; Cole, A. L. J.; Munro, M. H. G. J. Nat. Prod. 2004, 67, 2090-2092.
6. 7b
7. (a) Seya, H.; Nozawa, K.; Udagawa, S.; Nakajima, S.; Kawai, K. Chem. Pharm. Bull. 1986, 34, 2411-2416.
8. (b) Casnati, G.; Pochini, A.; Ungaro, R. Gazz. Chim. Ital. 1973, 103, 141-151.
9. Julian, P. L.; Pikl, J.; Boggess, D. J. Am. Chem. Soc. 1934, 56, 1797-1801.
10. Adhikari, S.; Caillé, S.; Hanbauer, M.; Ngo, V. X.; Overman, L. E. Org. Lett. 2005, 7, 2795-2798.
11. Mukaiyama, T.; Banno, K.; Narasaka, K. J. Am. Chem. Soc. 1974, 96, 7503-7509.
12. Garner, P.; Park, J. M. Organic Syntheses; Wiley: New York, 1998; Collect. Vol. IX, pp 300-305.
13. (a) The acid sensitivity of 3-hydroxypyrrolidinoindolines is believed to derive from acid-catalyzed ring opening of the aminal functionality, Iminium species generated in this way could degrade by multiple pathways, for example, by retroaldol-type cleavage.
14. 13b demonstrated the instability of the 3-hydroxypyrrolidinoindoline subunit under strongly basic conditions or upon reaction with triphenylphosphine.
15. (a) Minato, H.; Matsumoto, M.; Katayama, T. J. Chem. Soc., Perkin Trans. 1 1973, 1819-1825.
16. (b) Takahashi, C.; Numata, A.; Ito, Y.; Matsumura, E.; Araki, H.; Iwaki, H.; Kushida, K. J. Chem. Soc., Perkin Trans. 1 1994, 1859-1864.
17. (a) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753-1765.
18. (b) Rychnovsky, S. D.; Kim, J. Tetrahedron Lett. 1991, 32, 7219-7222.
19. The use of excess TBAF resulted in lower yields.
20. (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156.
21. (b) Meyer, S. D.; Schreiber, S. L. J. Org. Chem. 1994, 59, 7549-7552.
22. (a) Bal, B. S.; Childers, W. E., Jr.; Pinnick, H. W. Tetrahedron 1981, 37, 2091-2096.
23. (b) Kraus, G. A.; Taschner, M. J. J. Org. Chem. 1980, 45, 1175-1176.
24. BOP = benzotriazole-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate.
25. Depew, K. M.; Marsden, S. P.; Zatorska, D.; Zatorski, A.; Bornmann, W. G.; Danishefsky, S. J. J. Am. Chem. Soc. 1999, 121, 11953-11963.
26. The C3 acetate analogue of 13 provided single crystals allowing the relative configuration of this intermediate to be confirmed by X-ray crystallography.
27. The substituent was OAc or OTIPS instead of OMe.
28. (a) Makino, S.; Nakanishi, E.; Tsuji, T. Synlett 2003, 6, 817-820.
29. (b) Bailey, P. D.; Bannister, N.; Bernad, M.; Blanchard, S.; Boa, A. N. J. Chem. Soc., Perkin Trans. 1 2001, 3245-3251.
30. Mulliez, M.; Royer, J. Tetrahedron 1984, 40, 5143-5151.
31. 25 A summary of peak assignments for synthetic gliocladin C, which were established by HMQC and HMBC experiments, can be found in the Supporting Information.
32. Usami, Y. Personal communication, Aug 8, 2006.
33. Anthoni, U.; Christophersen, C.; Nielsen, P. H. Naturally Occurring Cyclotryptophans and Cyclotryptamines. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon: New York, 1999; Vol. 13, pp 163-236.