The Suzuki-Miyaura reaction in the chemical transformations of vindoline.

Joanna Ruszkowska; Robert Chrobak; Paweł Zero; Jan K Maurin; Joanna Szawkało; Zbigniew Czarnocki

doi:10.18388/abp.2007_3188

The Suzuki-Miyaura reaction in the chemical transformations of vindoline.

Joanna Ruszkowska Faculty of Chemistry, Warsaw University, Warszawa, Poland.;
Robert Chrobak
Paweł Zero
Jan K Maurin
Joanna Szawkało
Zbigniew Czarnocki

DOI: https://doi.org/10.18388/abp.2007_3188

Abstract

Vindoline and its analogues are important constituents of the Madagascan periwinkle Catharanthus roseus, and some of them are valuable chemotherapy drugs used in treatment for some types of cancer, including leukaemia, lymphoma, breast and lung cancer. The search for semi-synthetic congeners of natural substances is still an important task for organic chemistry. In this communication we report the synthesis of five new vindoline derivatives, 15-(2-methoxyphenyl)vindoline 11, 15-(3-methoxyphenyl)vindoline 12, 15-(2-nitrophenyl)vindoline 13, 15-(3-cyanophenyl)vindoline 15, and 15-(4-cyanophenyl)vindoline 16 using the Suzuki-Miyaura reaction as the key step. X-Ray analysis of compound 16 is also reported.

Published

2007-12-08

Issue

Vol. 54 No. 4 (2007)

Section

Articles

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