+ Translate

Preparation of steroidal 5 beta 6 beta epoxides and their oxidation by chromium trioxide

, : Preparation of steroidal 5 beta 6 beta epoxides and their oxidation by chromium trioxide. Journal of the Chemical Society Perkin Transactions I (7): 2001-2004

Reaction of 3.alpha.-chloroandrost-5-en-17-one with m-chloroperbenzoic acid affords the 5.beta.,6.beta.-epoxide. This is accomplished by some Baeyer-Villiger oxidation at C-17. The 3.alpha.-chlorine atom can be removed by hydrogenolysis with tributyltin hydride. Although the unsubstituted 5.beta.,5.beta.-epoxide is oxidized by chromium trioxide to the 5.alpha.-hydroxy 6-ketone, the 3.alpha.-chloro 5.beta.,6.beta.-epoxide is unreactive.

(PDF 0-2 workdays service)

Accession: 006173970

Submit PDF Full Text: Here

Submit PDF Full Text

No spam - Every submission is manually reviewed

Due to poor quality, we do not accept files from Researchgate

Submitted PDF Full Texts will always be free for everyone
(We only charge for PDFs that we need to acquire)

Select a PDF file:

Related references

Flaih N.; Hanson J.R.; Hitchcock P.B., 1991: Neighboring group participation in the chromium trioxide oxidation of steroidal 4 5 epoxides x ray molecular structure of 4 beta 6 beta 17 beta triacetoxy 3 beta 5 alpha dihydroxyandrostane. Chromium trioxide oxidation of steroidal 3.beta.-acetoxy-4.alpha.-5.alpha.-epoxides affords products in which the acetoxy group has migrated to the 4.beta.-position whilst oxidation of the isomeric 4.beta.,5.beta.-epoxides affords 5.alpha.-hydroxy...

Centurión, O.M.; Galagovsky, L.R.; Gros, E.G., 1995: Cleavage reaction of 5 beta, 6 beta steroidal epoxides carrying different groups at C-3. The particular behavior of 5 beta, 6 beta steroidal epoxides carrying different groups at C-3 was studied. These epoxides may exhibit different cleavage behavior according to the nature of the solvent, the acid-base state of the medium, and the le...

Roth, H.J., 1959: Aminolysis of epoxides. III. Preparation of beta-hydroxyalkyl-dimethyl-purines; double decomposition of theophylline & theobromine with 1,2-epoxides. Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft 292/64(5): 234-238

Watabe, T.; Komatsu, T.; Kobayashi, K.; Isobe, M.; Ozawa, N.; Saitoh, Y., 1985: The obligatory intermediacy of 16,17 alpha- and 16,17 beta-epoxides in the biotransformation of androsta-5,16-dien-3 beta-ol to androst-5-ene-3 beta, 16 alpha, 17 beta- and -3 beta, 16 beta, 17 alpha-triols by male rat liver microsomes. The C16-double bond of the biolefinic steroid, androsta-5,16-dien-3 beta-ol (delta 16-ANDO), was regioselectively oxidized by male rat liver microsomes in the presence of NADPH and EDTA to 16 alpha, 17 alpha-epoxyandrost-5-en-3 beta-ol (delta 16-A...

Waldmann, D.; Schreier, P., 1995: Stereochemical studies of epoxides formed by lipoxygenase-catalyzed co-oxidation of retinol, beta-ionone, and 4-hydroxy-beta-ionone. High-pressure liquid chromatographic (HPLC) analysis of the products formed during co-oxidation of retinol (1), beta-ionone (2), and 4-hydroxy-beta-ionone (3) by purified soybean lipoxygenase isoenzymes (LOX-1/LOX-2) revealed 5,6-epoxides as major...

Watanabe H.; Kawanishi T.; Miyamoto K.; Kubodera N.; Sasahara K.; Ochi K., 1992: Novel procedure for the preparation of tritiated 1 alpha 3 beta dihydroxy 2 beta steroidal compounds. During the course of our development of 20(S)-(3-hydroxy-3-methylbutyloxy)-9,10-secopregna-5,7,10(19)-triene-1.alpha.,3.beta.-diol (22-oxacalcitriol) as an antihyperparathyroidism agent, tritiated 22-oxacalcitriol was needed for pharmakokinetic an...

Watanabe, H.; Kawanishi, T.; Miyamoto, K.; Kubodera, N.; Sasahara, K.; Ochi, K., 1992: Novel procedure for the preparation of 1 alpha,3 beta-dihydroxy-2 beta-tritiated steroidal compounds. Steroids 57(9): 444-446

Kennedy, T.A.; Liebler, D.C., 1991: Peroxyl radical oxidation of beta-carotene: formation of beta-carotene epoxides. A chemical model system was used to study peroxyl radical trapping reactions of beta-carotene (1) that may contribute to its antioxidant action in biological systems. Peroxyl radicals generated in hexane by thermolysis of azobis(2,4-dimethylvalero...

Casals-Stenzel, J.; Buse, M.; Wambach, G.; Losert, W., 1984: The renal action of spirorenone and other 6 beta,7 beta; 15 beta,16 beta-dimethylene-17-spirolactones, a new type of steroidal aldosterone antagonists. The aldosterone antagonistic activity in vivo and the affinity for mineralocorticoid receptors (MCR) in vitro of 3-(17 beta-hydroxy-6 beta,7 beta; 15 beta,16 beta-dimethylene-3-oxo-1, 4-androstadiene-17 alpha-yl) propionic acid gamma-lactone (spir...

Bull J.R.; Van Zyl C.J., 1972: Steroidal analogues of unnatural configuration part 5 transformations of 5 6 beta epoxy 4 4 14 beta trimethyl 19 10 greater than 9 beta abeo 5 beta 10 alpha pregnan 11 one. Tetrahedron 28(14): 3957-3967