- The hydroxylation and amidation of equilenin acetate catalyzed by chloro[5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato]manganese(III)
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The aromatic steroid equilenin acetate undergoes regioselective and stereoselective hydroxylation and amidation catalyzed by a manganese porphyrin using iodosobenzene (PhIO) and N-tosyliminophenyliodinane (PhINTs) as the oxygen and nitrogen donor, respectively.
- Yang, Jerry,Weinberg, Richard,Breslow, Ronald
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- Regioselective oxidations of equilenin derivatives catalyzed by a rhodium(III) porphyrin complex - Contrast with the manganese(III) porphyrin
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Equilenin acetate and dihydroequilenin acetate were oxidized with iodosobenzene and a rhodium(III) porphyrin catalyst. The selectivity of the reactions differs from that with the corresponding Mn(III) catalyst, or from that of free radical chain oxidation. (C) 2000 Published by Elsevier Science Ltd.
- Yang,Breslow
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- An effective approach to B-ring aromatization of equilin
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Epoxidation of equilin followed by rearrangement-elimination catalyzed by either proton acids or Lewis acids generates an estrogen with an aromatic B-ring. This procedure represents an effective method for the conversion of an equilin nucleus to an equilenin nucleus.
- Cao, Zhisong,Liehr, Joachim G.
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p. 145 - 155
(2007/10/03)
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- Ketol Formation by Peracid Oxidation of Tricyclic Styrene
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Oxidation of 17β-hydroxy-5-methoxy-de-A-oestra-5,7,9,14-tetraene (1) with m-chloroperbenzoic acid or monoperphthalic acid yields the epimeric ketols, 14α- and 14β,17β-dihydroxy-5-methoxy-de-A-oestra-5,7,9-trien-15-one, (2) and (3) in ratio of 6:1.The configurations at C-14 of these ketols were assigned by 1H n.m.r. spectral comparison with AB-aromatic steroids, and the structure of the major product (2) was confirmed by an X-ray crystallographic analysis.The 14α-ketol (2) gives the 17β-acetate (14) with acetic anhydride in pyridine, whereas the 14β-ketol (3) gives the 16-en-15-one (15)
- Cox, Philip J.,Howie, R. Alan,Nowicki, Alexander W.,Turner, Alan B.
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p. 657 - 664
(2007/10/02)
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