Attempted Synthesis of Vinca Alkaloids Condensed with Three-Membered Rings

被引:7
|
作者
Keglevich, Andras [1 ,2 ]
Mayer, Szabolcs [1 ,2 ]
Papai, Reka [3 ,4 ]
Szigetvari, Aron [5 ,6 ]
Santa, Zsuzsanna [5 ,6 ]
Dekany, Miklos [5 ,6 ]
Szantay, Csaba, Jr. [5 ,6 ]
Keglevich, Peter [1 ,2 ]
Hazai, Laszlo [1 ,2 ]
机构
[1] Univ Technol & Econ, Dept Organ Chem & Technol, H-1111 Budapest, Hungary
[2] Gellert Ter 4, H-1111 Budapest, Hungary
[3] ComInnex Inc, Graphisoft Pk,Bldg D, H-1031 Budapest, Hungary
[4] Zahony U 7, H-1031 Budapest, Hungary
[5] Gedeon Richter Plc, Spectroscop Res Dept, H-1475 Budapest, Hungary
[6] 10,POB 27, H-1475 Budapest, Hungary
来源
MOLECULES | 2018年 / 23卷 / 10期
关键词
halogencyclopropane; dichlorocarbene; epoxidation; vindoline; catharanthine; dimer alkaloids; vindoline trimer; BISINDOLE ALKALOIDS; CATHARANTHUS-ROSEUS; CYCLOPROPANE RING; VINBLASTINE; HYDROXYINDOLENINE; ANALOGS;
D O I
10.3390/molecules23102574
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Our successful work for the synthesis of cyclopropanated vinblastine and its derivatives by the Simmons-Smith reaction was followed to build up further three-membered rings into the 14,15-position of the vindoline part of the dimer alkaloid. Halogenated 14,15-cyclopropanovindoline was prepared by reactions with iodoform and bromoform, respectively, in the presence of diethylzinc. Reactions of dichlorocarbene with vindoline resulted in the 10-formyl derivative. Unexpectedly, in the case of the dimer alkaloids vinblastine and vincristine, the rearranged products containing an oxirane ring in the catharanthine part were isolated from the reactions. The attempted epoxidation of vindoline and catharanthine also led to anomalous rearranged products. In the epoxidation reaction of vindoline, an o-quinonoid derivative was obtained, in the course of the epoxidation of catharanthine, a hydroxyindolenine type product and a spiro derivative formed by ring contraction reaction, were isolated. The coupling reaction of vindoline and the spiro derivative obtained in the epoxidation of catharanthine did not result in a bisindole alkaloid. Instead, two surprising vindoline trimers were discovered and characterized by NMR spectroscopy and mass spectrometry.
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页数:21
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