A short, scalable synthesis of the carbocyclic core of the anti-angiogenic cortistatins from (+)-estrone by B-ring expansion

Organic Letters

Volumn 10, Issue 22, 2008, Pages 5247-5250

  Kürti, László ^a   Czakó, Barbara ^a   Corey, E J ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANGIOGENESIS INHIBITOR; CARBOXYLIC ACID; CORTISTATIN; ESTRONE; NEUROPEPTIDE;

ARTICLE; CHEMISTRY; ENZYME SPECIFICITY; STEREOISOMERISM; SYNTHESIS;

ACIDS, CARBOCYCLIC; ANGIOGENESIS INHIBITORS; ESTRONE; NEUROPEPTIDES; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 58049215941     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802328n     Document Type: Article

References (24)

1. Aoki, S.; Watanabe, Y.; Sanagawa, M.; Setiawan, A.; Kotoku, N.; Kobayashi, M. J. Am. Chem. Soc. 2006, 128, 3148-3149.
2. (a) Aoki, S.; Watanabe, Y.; Tanabe, D.; Setiawan, A.; Arai, M.; Kobayashi, M. Tetrahedron Lett. 2007, 48, 4485-4488.
3. (b) Watanabe, Y.; Aoki, S.; Tanabe, D.; Setiawan, A.; Kobayashi, M. Tetrahedron 2007, 63, 4074-4079.
4. Folkman, J. N. Engl. J. Med. 1971, 285, 1182-1186.
5. For recent total syntheses of (+)-cortistatin A, see: (a) Shenvi, R. A.; Guerrero, C. A.; Shi, J.; Li, C.-C.; Baran, P. S. J. Am. Chem. Soc. 2008, 130, 7241-7243.
6. (b) Nicolaou, K. C.; Sun, Y.-P.; Peng, X.-S.; Polet, D.; Chen David, Y. K. Angew. Chem., Int. Ed. 2008, 47, 7310-7313.
7. For other studies toward the synthesis of cortistatins, see: (c) Simmons, E. M.; Hardin, A. R.; Guo, X.; Sarpong, R. Angew. Chem., Int. Ed. 2008, 47, 6650-6653.
8. (d) Yamashita, S.; Iso, K.; Hirama, M. Org. Lett. 2008, 10, 3413-3415.
9. (a) Yeung, Y.-Y.; Chein, R.-J.; Corey, E. J. J. Am. Chem. Soc. 2007, 129, 10346-10347.
10. (b) Canales, E.; Corey, E. J. Org. Lett. 2008, 10, 3271-3273.
11. (c) Hu, Q.-Y.; Rege, P. D.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 5984-5986.
12. Brown, W.; Findlay, J. W. A.; Turner, A. B. Chem. Commun. 1968, 10, 11.
13. (a) Rickborn, B.; Gerkin, R. M. J. Am. Chem. Soc. 1968, 90, 4193-4194.
14. (b) Rickborn, B.; Gerkin, R. M. J. Am. Chem. Soc. 1971, 93, 1693-1700.
15. Lemaire, M.; Doussot, J.; Guy, A. Chem. Lett. 1988, 1581-1584.
16. For a review on the Demjanov and Tiffeneau-Demjanov rearrangements, see: Smith, P. A. S.; Baer, D. R. Org. React. 1960, 11, 157-188.
17. Wang, Z.; Yang, D.; Mohanakrishnan, A. K.; Fanwick, P. E.; Nampoothiri, P.; Hamel, E.; Cushman, M. J. Med. Chem. 2000, 43, 2419-2429.
18. (a) Pribluda, V. S.; Green, S. J. Science (Washington, D.C.) 1998, 280, 987-988.
19. (b) Edsall, A. B.; Mohanakrishnan, A. K.; Yang, D.; Fanwick, P. E.; Hamel, E.; Hanson, A. D.; Agoston, G. E.; Cushman, M. J. Med. Chem. 2004, 47, 5126-5139.
20. (a) Galantay, E.; Weber, H. P. Experientia 1969, 25, 571-572.
21. (b) Groen, M. B.; Zeelen, F. J. Recl.: J. R. Neth. Chem. Soc. 1984, 103, 169-173.
22. For the preparation of compound 18 in small quantities, see: Abushanab, E.; Lee, D.-Y.; Meresak, W. A.; Duax, W. L. J. Org. Chem. 1976, 41, 1601-1603.
23. For the strucutural elucidation of compound 18, see: Weeks, C. M.; Rohrer, D. C.; Duax, W. L.; Abushanab, E. Steroids 1976, 27, 261-268.
24. Compound 18 was obtained as a >7:1 mixture of diastereomers at C9. Distereomerically pure 18 is obtained after crystallization from pentane/ether.