Synthesis of C-15 vindoline analogues by palladium-catalyzed cross-coupling reactions
Synthesis of C-15 vindoline analogues by palladium-catalyzed cross-coupling reactions
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DOI：
10.1021/jo061243y
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发表时间：
2006-09-29
影响因子：
3.6
通讯作者：
Rawal, Viresh H.
中科院分区：
文献类型：
--
作者：
Johnson, Peter D.;Sohn, Jeong-Hun;Rawal, Viresh H.
描述了使用钯催化的交叉偶联反应快速构建文多灵的各种C-15-取代的类似物的一般方案。文多灵分别与N-溴代琥珀酰亚胺或N-碘代琥珀酰亚胺反应，高产率地制备了所需的溴代和碘代文多灵。该研究不仅导致了一些结构新颖的文多灵类似物的制备，而且为长春碱，长春新碱和相关抗癌药物的合成开辟了新的策略。还描述了对映体-他勃松宁向对映体-文多灵的转化。
Described are general protocols for the rapid construction of various C-15-substituted analogues of vindoline using palladium-catalyzed cross-coupling reactions. The required bromo- and iodovindolines were prepared in high yield by the reaction of vindoline withN-bromosuccinimide orN-iodosuccinimide, respectively. The study not only led to the preparation of a number of structurally novel vindoline analogues but also opens the door to new strategies for the synthesis of vinblastine, vincristine, and related anticancer agents. Also described is the conversion ofent-tabersonine toent-vindoline.