α-Hydroxylation at C-15 and C-16 in Cholesterol: Synthesis of (25R)-5α-Cholesta-3β,15α,26-triol and (25R)-5α-Cholesta- 3β,16α,26-triol from Diosgenin

Organic Letters

Volumn 6, Issue 2, 2004, Pages 269-271

  Williams, John R ^a   Gong, Hua ^a   Hoff, Nathan ^a   Olubodun, Olaoluwa I ^a   Carroll, Patrick J ^b  

^a Temple University   (United States)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5ALPHA CHOLESTA 3BETA,15ALPHA,26 TRIOL; 5ALPHA CHOLESTA 3BETA,16ALPHA,26 TRIOL; 5ALPHA CHOLESTA 3BETA,16BETA,26 TRIOL; CHOLESTEROL DERIVATIVE; DIOSGENIN; HYDROXYL GROUP; KETONE; STEROID; UNCLASSIFIED DRUG;

ARTICLE; CHOLESTEROL SYNTHESIS; DRUG SYNTHESIS; HYDROXYLATION; METHODOLOGY; REDUCTION;

CHOLESTEROL; CRYSTALLOGRAPHY, X-RAY; DIOSGENIN; HYDROXYCHOLESTEROLS; HYDROXYLATION; MODELS, MOLECULAR; MOLECULAR CONFORMATION;

EID: 0842328411     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036257u     Document Type: Article

References (20)

1. Schroepfer, G. J., Jr. Physiol. Rev. 2000, 80, 361.
2. Minale, L.; Ricco, R.; Zollo, F. In Prog. Chem. Org. Nat. Prod.; Herz, W., Kirby, G. W., Moore, R. E., Steglich, W., Tamm, Ch., Eds.; Springer-Verlag: New York, 1993, 62, 75.
3. (a) Tachibana, K.; Sakaitani, M.; Nakanishi, K. Science 1984, 226, 703.
4. (b) Tachibana, K.; Sakaitani, M.; Nakanishi, K. Tetrahedron 1985, 41, 1027.
5. Miyaoka, H.; Shinohara, M.; Shimomura, M.; Mitome, H.; Yano, A.; Iguchi, K.; Yamada, Y. Tetrahedron 1997, 53, 5403.
6. Breslow, R.; Baldwin, S.; Flechtner, T.; Kalicky, P.; Liu, S.; Washburn, W. J. Am. Chem. Soc. 1973, 95, 3251.
7. For a recent reference, see: Yang, J.; Gabriele, B.; Belvedere, S.; Huang, Y.; Breslow, R. J. Org. Chem. 2002, 67, 5057.
8. Taylor, E. J.; Djerassi, C. J. Org. Chem. 1977, 42, 3571.
9. Marino, J. P.; Abe, H. J. Am. Chem. Soc. 1981, 103, 2907.
10. Izzo, I.; Filippo, M. D.; Napolitano, R.; De Riccardis, F. Eur. J. Org. Chem. 1999, 3505.
11. Williams, J. R.; Chai, D.; Bloxton, J. D., II; Gong, H.; Solvibile, W. R. Tetrahedron 2003, 59, 3183.
12. Williams, J. R.; Chai, D.; Wright, D. Steroids 2002, 67, 1041.
13. Kim, H. S.; Oh, S. H. Biol. Med. Org. Chem. Lett. 1993, 3, 1339.
14. Giner, J. L.; Margot, C.; Djerassi, C. J. Org. Chem. 1989, 54, 369.
15. For reviews see: (a) Mitsunobu, O. Synthesis 1981, 1. (b) Hughes, D. L. Org. Prep. Procd. Int. 1996, 28, 127.
16. For reviews see: (a) Mitsunobu, O. Synthesis 1981, 1. (b) Hughes, D. L. Org. Prep. Procd. Int. 1996, 28, 127.
17. Dodge, J. A.; Trujillo, J. I.; Presnell, M. J. Org. Chem. 1994, 59, 234.
18. Ronchetti, F.; Russo, G. J. Labelled Compd. Radiopharm. 1978, 14, 687.
19. (a) Luche, J.-L. J. Am. Chem. Soc. 1978, 100, 2226.
20. (b) Gemal, A. L.; Luche, J.-L. J. Am. Chem. Soc. 1981, 103, 5454.