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Abstract:

Two strategies have been explored for the synthesis of steroidal 20,16- γ-carbolactones from the corresponding 17-ketoandrostane. A highly efficient, stereospecific protocol has been developed for the β-oriented cis-γ-lactone, based on a Michael addition of cyanide to a conjugated ketone. A different approach, involving prior attachment of a 3-carbon side chain on C-17 of a 17-oxo-16β-acetoxy-androstane led to the epimeric, α- oriented lactone.

Registro:

Documento: Artículo
Título:Stereospecific synthesis of steroidal 20,16-γ-carbolactones
Autor:Bruttomesso, A.C.; Doller, D.; Gros, E.G.
Filiación:Depto. de Quím. Orgán., Fac. de Ciencias Exactas y Naturales, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Schering-Plough Research Institute, 2015 Galloping Hill Road, Kenilworth, NJ 07033, United States
Palabras clave:20,16 gamma carbolactone derivative; androstane derivative; lactone derivative; unclassified drug; article; drug structure; drug synthesis; nuclear Overhauser effect; stereospecificity
Año:1998
Volumen:28
Número:21
Página de inicio:4043
Página de fin:4057
DOI: http://dx.doi.org/10.1080/00397919808004965
Título revista:Synthetic Communications
Título revista abreviado:Synth. Commun.
ISSN:00397911
CODEN:SYNCA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00397911_v28_n21_p4043_Bruttomesso

Referencias:

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Citas:

---------- APA ----------
Bruttomesso, A.C., Doller, D. & Gros, E.G. (1998) . Stereospecific synthesis of steroidal 20,16-γ-carbolactones. Synthetic Communications, 28(21), 4043-4057.
http://dx.doi.org/10.1080/00397919808004965
---------- CHICAGO ----------
Bruttomesso, A.C., Doller, D., Gros, E.G. "Stereospecific synthesis of steroidal 20,16-γ-carbolactones" . Synthetic Communications 28, no. 21 (1998) : 4043-4057.
http://dx.doi.org/10.1080/00397919808004965
---------- MLA ----------
Bruttomesso, A.C., Doller, D., Gros, E.G. "Stereospecific synthesis of steroidal 20,16-γ-carbolactones" . Synthetic Communications, vol. 28, no. 21, 1998, pp. 4043-4057.
http://dx.doi.org/10.1080/00397919808004965
---------- VANCOUVER ----------
Bruttomesso, A.C., Doller, D., Gros, E.G. Stereospecific synthesis of steroidal 20,16-γ-carbolactones. Synth. Commun. 1998;28(21):4043-4057.
http://dx.doi.org/10.1080/00397919808004965