A biomimetic approach to C-nor-D-homo-steroids

Journal of the American Chemical Society

Volumn 132, Issue 29, 2010, Pages 9968-9969

  Heretsch, Philipp ^a   Rabe, Sebastian ^a   Giannis, Athanassios ^a  

^a UNIVERSITY OF LEIPZIG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

NATURAL PRODUCTS;

BIOMIMETICS;

LIPIDS;

CYCLOPAMINE; HOMOSTEROID; NAKITERPIOSIN; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; BIOMIMETICS; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; SYNTHESIS;

BIOLOGICAL AGENTS; BIOMIMETICS; HOMOSTEROIDS; KINETICS; SUBSTRATE SPECIFICITY;

EID: 77955811141     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja103152k     Document Type: Article

References (23)

1. Li, H.-J.; Jiang, Y.; Li, P. Nat. Prod. Rep. 2006, 23, 735-752.
2. Heretsch, P.; Tzagkaroulaki, L.; Giannis, A. Angew. Chem., Int. Ed. 2010, 49, 3418-3427, and citations therein.
3. Gao, S.; Wang, Q.; Huang, L. J.-S.; Lum, L.; Chen, C. J. Am. Chem. Soc. 2010, 132, 371-383.
4. Guile, S. D.; Saxton, J. E.; Thornton-Pett, M. J. Chem. Soc., Perkin Trans. 1 1992, 1763-1767.
5. Brown, E.; Lebreton, J. Tetrahedron 1987, 43, 5827-5840.
6. (a) Hirschmann, R.; Snoddy, C. S., Jr.; Wendler, N. L. J. Am. Chem. Soc. 1952, 74, 2693-2694.
7. (b) Hiskey, C. F.; Hirschmann, R.; Wendler, N. L. J. Am. Chem. Soc. 1953, 75, 5135-5136.
8. (c) Hirschmann, R.; Snoddy, C. S., Jr.; Hiskey, C. F.; Wendler, N. L. J. Am. Chem. Soc. 1954, 76, 4013-4025.
9. Kaneko, K.; Mitsuhashi, H.; Hirayama, K.; Yoshida, N. Phytochemistry 1970, 9, 2489-2495.
10. (a) Giannis, A.; Heretsch, P.; Sarli, V.; Stossel, A. Angew. Chem., Int. Ed. 2009, 48, 7911-7914.
11. (b) Heretsch, P.; Rabe, S.; Giannis, A. Org. Lett. 2009, 11, 5410-5412.
12. (a) Mitsuhashi, H.; Shimizu, Y. Tetrahedron 1963, 19, 1027-1035.
13. (b) Mitsuhashi, H.; Shibata, K.; Sato, T.; Shimizu, Y. Chem. Pharm. Bull. 1964, 12, 1-5.
14. Comins, D. L.; Dheghani, A. Tetrahedron Lett. 1992, 33, 6299-6302.
15. McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1983, 24, 979-982.
16. Solvents that gave no or a very slow reaction: benzene, dichloroethane, nitromethane, n-octane; solvents that gave similar or slightly lower yields: chlorobenzene, pyridine, xylenes.
17. Fu, X.; Chan, T.-M.; Tann, C.-H.; Thiruvengadam, T. K. Steroids 2002, 67, 549-554.
18. 2at high temperatures has been reported: Ferrari, T.; Vogel, P. Synlett 1991, 233-234.
19. Schönecker, B.; Zheldakova, T.; Liu, Y.; Kötteritzsch, M.; Günther, W.; Görls, H. Angew. Chem., Int. Ed. 2003, 42, 3240-3244.
20. (a) Johns, W. F.; Salamon, K. W. J. Org. Chem. 1979, 44, 958-961.
21. (b) Green, M. J.; Abraham, N. A.; Fleischer, E. B.; Case, J.; Fried, J. Chem. Commun. 1970, 234-235.
22. (c) Johnson, W. S.; Cox, J. M.; Graham, D. W.; Whitlock, H. W., Jr. J. Am. Chem. Soc. 1967, 89, 4524-4526.
23. Marko, I. E.; Ates, A.; Gautier, A.; Leroy, B.; Plancher, J.-M.; Quesnel, Y.; Vanherck, J.-C. Angew. Chem., Int. Ed. 1999, 38, 3207-3209.