The Suzuki-Miyaura reaction in the chemical transformations of vindoline.
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.
Ruszkowska
Joanna
J
Faculty of Chemistry, Warsaw University, Warszawa, Poland.
Chrobak
Robert
R
Zero
Paweł
P
Maurin
Jan K
JK
Szawkało
Joanna
J
Czarnocki
Zbigniew
Z
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D014747:Vinblastine / Q000031:analogs & derivatives* / Q000737:chemistry
D000972:Antineoplastic Agents, Phytogenic; C009667:vindoline; D014747:Vinblastine