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Titolo:
A highly efficient, stereoselective oxyfunctionalization of unactivated carbons in steroids with dimethyldioxirane
Autore:
Iida, T; Yamaguchi, T; Nakamori, R; Hikosaka, M; Mano, N; Goto, J; Nambara, T;
Indirizzi:
Nihon Univ, Coll Humanities & Sci, Dept Chem, Setagaya Ku, Tokyo 1568550, Japan Nihon Univ Tokyo Japan 1568550 t Chem, Setagaya Ku, Tokyo 1568550, Japan Tohoku Univ, Grad Sch Pharmaceut Sci, Sendai, Miyagi 9818578, Japan TohokuUniv Sendai Miyagi Japan 9818578 ci, Sendai, Miyagi 9818578, Japan Hoshi Univ, Tokyo 1478501, Japan Hoshi Univ Tokyo Japan 1478501Hoshi Univ, Tokyo 1478501, Japan
Titolo Testata:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
fascicolo: 18, , anno: 2001,
pagine: 2229 - 2236
SICI:
1472-7781(20010921):18<2229:AHESOO>2.0.ZU;2-E
Fonte:
ISI
Lingua:
ENG
Soggetto:
C-H BONDS; SATURATED-HYDROCARBONS; CHOLESTANE DERIVATIVES; RUTHENIUM PORPHYRINS; SELECTIVE OXIDATION; FUNCTIONALIZATION; HYDROXYLATION; DIOXIRANES; CHEMISTRY; ACIDS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
33
Recensione:
Indirizzi per estratti:
Indirizzo: Iida, T Nihon Univ, Coll Humanities & Sci, Dept Chem, Setagaya Ku, Tokyo 1568550, Japan Nihon Univ Tokyo Japan 1568550 Setagaya Ku, Tokyo 1568550, Japan
Citazione:
T. Iida et al., "A highly efficient, stereoselective oxyfunctionalization of unactivated carbons in steroids with dimethyldioxirane", J CHEM S P1, (18), 2001, pp. 2229-2236

Abstract

Oxyfunctionalization of unactivated methine carbon atoms with dimethyldioxirane (DMDO) is studied for various substituted steroids related to the 5 beta -cholane and 5 alpha -cholestane series. A highly efficient, stereoselective, one-step remote oxidation of specific methine carbons is attained byDMDO oxidation under mild conditions to give a variety of novel mono- and dihydroxylated steroids. The reactivity and site selectivity of remote oxyfunctionalization is influenced significantly by the structural and steric environments as well as by the degree of electron density of the target methine carbon atoms in the molecules. The non-enzymatic procedure may be usefully applied to effective and short-step syntheses of bioactive steroids.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 11/07/20 alle ore 07:10:07