A comparative study of remote oxy-functionalization of unactivated carbonsin 5β-steroids by dimethyldioxirane and 2,6-dichloropyridineN-oxide/ruthenium-porphyrin/HBr

Arkivoc

Volumn 2003, Issue 8, 2003, Pages 171-179

  Iida, Takashi ^a   Ogawa, Shoujiro ^a   Shiraishi, Keisuke ^a   Kakiyama, Genta ^a   Goto, Takaaki ^b   Mano, Nariyasu ^b   Goto, Junichi ^b  

^a NIHON UNIVERSITY   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

2,6 dichloropyridine N oxide ruthenium porphyrin HBr; 5 steroids; Dimethyldioxirane; Hydroxylation; Ketonization; Remote oxy functionalization

Indexed keywords

(5,10,15,20 TETRAMESITYLPORPHYRINATE)RUTHENIUM CARBONYL COMPLEX; 2,6 DICHLOROPYRIDINE N OXIDE; 3 OXOX 5BETA CHOLAN O 24,20 LACTONE; 3ALPHA ACETOXY 5BETA HYDROXYCHOLAN O 24,20 LACTONE; 5BETA HYDROXY 3 OXOCHOLAN O 24,20 LACTONE; 5BETA STEROID; CHOLANE DERIVATIVE; DIMETHYLDIOXIRANE; FUNCTIONAL GROUP; HYDROBROMIC ACID; METHYL 17ALPHA HYDROXY 3 OXOCHOLAN 24 OATE; METHYL 3 OXO 4 CHOLEN 24 OATE; METHYL 3 OXO 5BETA CHOLAN 24 OATE; METHYL 3ALPHA 5BETA,17ALPHA DIHYDROXYCHOLAN 24 OATE; METHYL 3ALPHA ACETOXY 5BETA CHOLAN 24 OATE; METHYL 3ALPHA ACETOXY 5BETA HYDROXY 15 OXOCHOLAN 24 OATE; METHYL 3ALPHA ACETOXY 5BETA HYDROXYCHOLAN 24 OATE; METHYL 5BETA HYDROXY 3 OXOCHOLAN 24 OATE; METHYL 5BETA,14ALPHA DIHYDROXY 3 OXOCHOLAN 24 OATE; PYRIDINE DERIVATIVE; RUTHENIUM DERIVATIVE; STEROID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; COMPARATIVE STUDY; OXIDATION; STEREOCHEMISTRY;

EID: 3242667847     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (12)

1. Reese, P.B.; Steroids 2001, 66, 481.
2. Curci, R.; Dinoi, A; Rubino, M.F.; Pure Appl. Chem. 1995, 67, 811.
3. Iida, T.; Yamaguchi, T.; Nakamori, R.; Hikosaka, M.; Mano, N.; Goto, J.; Nambara, T.; J. Chem. Soc. Perkin 1 2001, 2229.
4. Iida, T.; Shiraishi, K.; Ogawa, S.; Goto, T.; Mano, N.; Goto, J.; Nambara, T; Lipids 2003, 38, 281.
5. Meunier, B.; Chem. Rev. 1992, 92, 1411.
6. Ohtake, H.; Higuchi, T.; Hirobe, M.; Heterocycles 1995, 40, 867.
7. Shingaki, T.; Miura, K.; Higuchi, T.; Hirobe, M.; Nagano, T.; Chem. Commun. 1997, 861.
8. Cérre, C.; Hofmann, A.F.; Schteingart, C.D.; Jia, W.; Maltby, D.; Tetrahedron 1997, 53, 435.
9. Rousseau, R.J.; Robins, R.K.; J. Heterocycles Chem. 1965, 2, 196.
10. Lindsey, J.S.; Schreiman, I.C.; Hsu, H.C.; Kearney, P.C; Marguerettaz, A.M.; J. Org. Chem. 1987, 52, 827.
11. Rillema, D.P.; Nagle, J.K.; Barringer, Jr., L.F.; Meyer, T.J.; J. Am. Chem. Soc. 1981, 103, 56.
12. Aranda, G.; Fetizon, M.; Tayeb, N.; Tetrahedron 1987, 43, 4147.