Conversion of an equilenane to the estrane: Synthesis of dl-3-methoxy-17β-carboxy-1,3,5(10)-estratriene

Banerjee, D.; Jacob, E.J.; Mahishi, Narain

doi:10.1016/s0039-128x(70)80151-9

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Organometallic Coupling1

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1974

1992

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Cited by 8 publications

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“…By a series of reductions it was transformed into 257, which was also synthesized from estrone [182]. In an attempt to incorporate a 17-oxygen, the condensation of 252 with 2-allyl-2-methyl-l,3-cyclopentanedione was attempted.…”

Section: Organometallic Couplingmentioning

confidence: 99%

Ab + D → Abd → Abcd

1974

Organic Chemistry: A Series of Monographs

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Section: Organometallic Couplingmentioning

confidence: 99%

Ab + D → Abd → Abcd

1974

Organic Chemistry: A Series of Monographs

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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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Contributions to organic synthesis and reaction mechanisms

Banerjee

1984

Proc. Indian Acad. Sci. (Chem. Sci.)

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Conversion of an equilenane to the estrane: Synthesis of dl-3-methoxy-17β-carboxy-1,3,5(10)-estratriene

Cited by 8 publications

References 10 publications

Ab + D → Abd → Abcd

Ab + D → Abd → Abcd

TheBirch Reduction of Aromatic Compounds

Contributions to organic synthesis and reaction mechanisms

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