15-Oxa-<i>D</i>-homosteroids

Ferland, Jean-Marie; Lefebvre, Y.

doi:10.1139/v84-055

Cited by 4 publications

(2 citation statements)

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“…Subjection of 20 to the previous reaction conditions (anhydrous m -CPBA and methanesulfonic acid) gave enedione 19 in 43% yield. The structure of 19 was confirmed by conversion to the known diketone 21 …”

mentioning

confidence: 91%

Oxidative Fragmentation of Pregna-14,16-dien-20-ones to 14β-Hydroxyandrost-15-en-17-ones

Fell

Heathcock²

2002

J. Org. Chem.

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Two methods have been developed for efficient conversion of pregna-14,16-dien-20-ones into 14 beta-hydroxyandrost-15-en-17-ones. One procedure consists of treatment of the ring-D dienone successively with sodium borohydride and singlet oxygen. The reaction is illustrated by the conversion of pregna-14,16-dien-20-one 1 into 14 beta-hydroxyandrost-15-en-17-one 3, via the corresponding allylic alcohol 2. Although this two-step procedure is simple, it provides 3 in relatively low yield, accompanied by a smaller amount of the isomeric 14 alpha-hydroxyandrost-15-en-17-one 6. An alternative one-step conversion is achieved by treatment of dienone 1 with a peroxyacid in the presence of a strong protic acid. This process is illustrated by the two-step conversion of dienone 1 into hydroxy ketone 11 in 51% overall yield (Scheme 5) and by the analogous conversion of dienone 13 into hydroxy ketone 24 in 61% overall yield (Scheme 11).

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mentioning

confidence: 91%

Oxidative Fragmentation of Pregna-14,16-dien-20-ones to 14β-Hydroxyandrost-15-en-17-ones

Fell

Heathcock²

2002

J. Org. Chem.

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“…[5] Zur Herstellung von rac-4 setzten wir den Aldehyd 3 in einer Barbier-Reaktion mit Allylbromid und Zink um. [15,16] Durch Vergleich der analytischen Daten mit den Literaturangaben [1a] konnte 2 als Ricciocarpin B identifiziert werden. katalysierte Hydrolyse von rac-5 ergab die besten Ergebnisse.…”

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Enantioselektive Synthese der Ricciocarpine A und B

2001

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TheBirch Reduction of Aromatic Compounds

Rabideau

Marcinow²

1992

Organic Reactions

131

138

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The reduction of aromatic compounds by alkali metals in liquid ammonia represents an important method for the preparation of partially unsaturated six‐membered rings. The reaction was discovered by Wooster and Godfrey, but the major development resulted from the efforts of A. J. Birch, and the reaction has since come to bear his name. Although a variety of metals can be used, the most common are sodium and lithium, and, to a lesser extent, potassium. Cosolvents such as ether or tetrahydrofuran (THF) are often used to improve solubility, and weak acids such as alcohols may be employed during the reaction as proton sources. The latter are necessary for the reduction of benzene and its unactivated derivatives. Improvement in experimental procedures by Wilds and Nelson, the application to polynuclear compounds by Hückel and later by Harvey, and the development of methods for the alkylation of the anions generated in this process (i.e., reductive alkylation) have made this reaction an important approach to the synthesis of a wide variety of organic compounds.

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15-Oxa-D-homosteroids

Abstract: , 315 (1984). On a prCparC des stCroides 15-oxa-D-homo dont les structures sont relikes celles des pregnanes et des estranes.

Cited by 4 publications

References 5 publications

Oxidative Fragmentation of Pregna-14,16-dien-20-ones to 14β-Hydroxyandrost-15-en-17-ones

Oxidative Fragmentation of Pregna-14,16-dien-20-ones to 14β-Hydroxyandrost-15-en-17-ones

Enantioselektive Synthese der Ricciocarpine A und B

TheBirch Reduction of Aromatic Compounds

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