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Synthesis of Vinca Alkaloids and Related Compounds, XV¹⁾ A New Synthetic Route to (+)-Vincaminic and (+)-Apovincaminic Esters

Lajos Szabó

Department of Organic Chemistry, Technical University, Budapest, XI. Gellért tér 4. H-1521, Hungary

Central Research Institute for Chemistry, Hungarian Academy of Sciences Budapest, II. Pusztaszeri ut 59/67, H-1525, Hungary

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György Kalaus,

György Kalaus

Department of Organic Chemistry, Technical University, Budapest, XI. Gellért tér 4. H-1521, Hungary

Central Research Institute for Chemistry, Hungarian Academy of Sciences Budapest, II. Pusztaszeri ut 59/67, H-1525, Hungary

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Csaba Szántay,

Corresponding Author

Csaba Szántay

Department of Organic Chemistry, Technical University, Budapest, XI. Gellért tér 4. H-1521, Hungary

Central Research Institute for Chemistry, Hungarian Academy of Sciences Budapest, II. Pusztaszeri ut 59/67, H-1525, Hungary

Department of Organic Chemistry, Technical University, Budapest, XI. Gellért tér 4. H-1521, HungarySearch for more papers by this author

Lajos Szabó,

Lajos Szabó

Department of Organic Chemistry, Technical University, Budapest, XI. Gellért tér 4. H-1521, Hungary

Central Research Institute for Chemistry, Hungarian Academy of Sciences Budapest, II. Pusztaszeri ut 59/67, H-1525, Hungary

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György Kalaus,

György Kalaus

Department of Organic Chemistry, Technical University, Budapest, XI. Gellért tér 4. H-1521, Hungary

Central Research Institute for Chemistry, Hungarian Academy of Sciences Budapest, II. Pusztaszeri ut 59/67, H-1525, Hungary

Search for more papers by this author

Csaba Szántay,

Corresponding Author

Csaba Szántay

Department of Organic Chemistry, Technical University, Budapest, XI. Gellért tér 4. H-1521, Hungary

Central Research Institute for Chemistry, Hungarian Academy of Sciences Budapest, II. Pusztaszeri ut 59/67, H-1525, Hungary

Department of Organic Chemistry, Technical University, Budapest, XI. Gellért tér 4. H-1521, HungarySearch for more papers by this author

First published: 1983

https://doi.org/10.1002/ardp.19833160709

Citations: 27

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Abstract

Esters of types 7 and 8, possessing excellent vasodilating effects, have been prepared. A method has been found for the resolution of methyl ester 7c. A new method is described for the preparation of the lactam (+)-10 and its conversion to the oxime (+)-11, from which (+)-vincamine (1a) and the (+)-apovincaminic esters 2a,b were synthesized.

Abstract

Über die Synthese von Vinca-Alkaloiden und verwandten Verbindungen, 15. Mitt.: Ein neuer Weg zur Synthese von (+)-Vincaminsäure- und (+)-Apovincaminsäureestern

Neue, beträchtliche gefäßweiternde Wirkung zeigende Verbindungen von Typ 7 und 8 wurden hergestellt und die Enantiomere des Methylesters 7c getrennt. Das mit der neuen Methode synthetisierte (+-10 Laktam und das (+)-11 Oxim lieferten das (+)-Vincamin (1a) und die (plus;)-Apovincaminsäureester 2a,b

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Volume316, Issue7

1983

Pages 629-638

Synthesis of Vinca Alkaloids and Related Compounds, XV¹⁾ A New Synthetic Route to (+)-Vincaminic and (+)-Apovincaminic Esters

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Synthesis of Vinca Alkaloids and Related Compounds, XV1) A New Synthetic Route to (+)-Vincaminic and (+)-Apovincaminic Esters

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Synthesis of Vinca Alkaloids and Related Compounds, XV¹⁾ A New Synthetic Route to (+)-Vincaminic and (+)-Apovincaminic Esters