Total synthesis of (-)-scabronine G, an inducer of neurotrophic factor production

Journal of the American Chemical Society

Volumn 127, Issue 39, 2005, Pages 13514-13515

  Waters, Stephen P ^a   Tian, Yuan ^a   Li, Yue Ming ^a   Danishefsky, Samuel J ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANONE; DITERPENOID; INTERLEUKIN 6; NATURAL PRODUCT; NERVE GROWTH FACTOR; NEUROTROPHIC FACTOR; SCABRONINE G; UNCLASSIFIED DRUG;

ACYLATION; ANNULATION REACTION; ARTICLE; CROSS COUPLING REACTION; DRUG SYNTHESIS; FRIEDEL CRAFTS REACTION; HYDROBORATION; MUSHROOM; SARCODON SCABROSUS;

DITERPENES; NERVE GROWTH FACTORS;

EID: 25844518482     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja055220x     Document Type: Article

References (26)

1. The scabronines are distinct from all other cyathanes by an angular C17 carboxyl group rather than C17 methyl: Kita, T.; Takaya, Y.; Oshima, Y.; Ohta, T.; Aizawa, K.; Hirano, T.; Inakuma, T. Tetrahedron 1998, 54, 11877.
2. Obara, Y.; Kobayashi, H.; Ohta, T.; Ohizumi, Y.; Nakahata, N. Mol. Pharmacol. 2001, 59, 1287.
3. (a) Hefti, F. Annu. Rev. Pharmacol. Toxicol. 1997, 37, 239.
4. (b) Luu, B.; de Aguilar, J.-L. G.; Girlanda-Junges, C. Molecules 2000, 5, 1439.
5. Dawbarn, D.; Allen, S. J. Neuropath. Appl. Neurobiol. 2003, 29, 211.
6. Kirik, D.; Georgievska, B.; Bjorklund, A. Nat. Neurosci. 2004, 7, 105.
7. (a) Pettus, T. R. R.; Inuoe, M.; Chen, X.-T.; Danishefslfy, S. J. J. Am. Chem. Soc. 2000, 122, 6160.
8. (b) Birman, V. B.; Danishefsky, S. J. J. Am. Chem. Soc. 2002, 124, 2080.
9. (c) Cho, Y. S.; Carcache, D. A.; Tian, Y.; Li, Y.-M.; Danishefsky, S. J. J. Am. Chem. Soc. 2004, 126, 14358.
10. To our knowledge, no synthetic efforts toward the scabronines have been reported. For recent syntheses of related cyathanes, see: (a) Snider, B. B.; Vo, N. H.; O'Neil, S. V.; Foxman, B. M. J. Am. Chem. Soc. 1998, 118, 1644.
11. (b) Piers, E.; Gilbert, M.; Cook, K. L. Org. Lett. 2000, 2, 1407.
12. (c) Takano, M.; Umino, A.; Nakada, M. Org. Lett. 2004, 6, 4897.
13. (d) Trost, B. M.; Dong, L.; Schroeder, G. M. J. Am. Chem. Soc. 2005, 127, 2844.
14. (a) Application of 3 to reach nonsteroidal terpenoids arose in the synthesis of longifolene: Corey, E. J.; Ohno, M.; Vatakencherry, P. A.; Mitra, R. B. J. Am. Chem. Soc. 1961, 83, 1251.
15. (b) For the synthesis of 3, see: Buchschacher, P.; Fürst, A.; Gutzwiller, J. Organic Syntheses; Wiley & Sons: New York, 1990; Collect. Vol. VII, p 368.
16. Nagata, W.; Mitsuru, Y.; Masayuk, M. J. Am. Chem. Soc. 1972, 94, 4644.
17. Ciceri, P.; Demnitz, F. W. J. Tetrahedron Lett. 1997, 38, 389.
18. McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1983, 24, 979.
19. (a) Ling, T.; Chowdhury, C.; Kramer, B. A.; Vong, B. G.; Palladino, M. A.; Theodorakis, E. A. J. Org. Chem. 2001, 66, 8843.
20. (b) For seminal work on reductive carboxylations of this type, see: Stork, G.; Rosen, P.; Goldman, N.; Coombs, R. V.; Tsuji, J. J. Am. Chem. Soc. 1965, 87, 275.
21. Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033.
22. Williams, J. M.; Jobson, R. B.; Yasuda, N.; Marchesini, G.; Dolling, U. H.; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36, 5461.
23. For a recent review, see: Pellissier, H. Tetrahedron 2005, 61, 6419.
24. Yu, W.; Jin, Z. Tetrahedron Lett. 2001, 42, 369. The aluminum enolate derived from Nagata addition did not react usefully with a variety of triflating agents, thus prompting recourse to the more reactive potassium enolate.
25. For a review, see: Negishi, E.-i. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York, 1998.
26. Guerrero, A.; Parrilla, A.; Camps, F. Tetrahedron Lett. 1990, 31, 1873.