APPLICATION OF A MODIFICATION OF POLONOVSKI REACTION TO SYNTHESIS OF VINBLASTINE-TYPE ALKALOIDS
APPLICATION OF A MODIFICATION OF POLONOVSKI REACTION TO SYNTHESIS OF VINBLASTINE-TYPE ALKALOIDS
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DOI：
10.1021/ja00438a046
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发表时间：
1976-01-01
影响因子：
15
通讯作者：
POTIER, P
中科院分区：
文献类型：
--
作者：
LANGLOIS, N;GUERITTE, F;POTIER, P
由修饰的Polonovski反应诱导的伊波甘衍生物的一个新的C(16)-C（21）骨架断裂，导致了具有天然C（16”）结构的蛇藤精衍生物的长春花碱型化合物的存在，这似乎是显著抗肿瘤活性所必需的。这种新的偶联方法与生物遗传途径相同，可用于部分合成天然玫瑰花抗肿瘤生物碱。圆二色性技术对该系列化合物具有很高的诊断价值，可以区分天然或非天然的C（16”）构型。在本研究中也遇到了C(5)-C(6)处的另一种类型的骨骼碎裂，在实验条件下被最小化。
A new C(16)-C(21) skeletal fragmentation of ibogane derivatives, induced by the modified Polonovski reaction, leads in the presence of aspidospermane derivatives to vinblastine-type compounds with the natural C(16'') configuration, which seems necessary for significant antitumor activity. This new method of coupling, which could be the same as the biogenetic pathway, was applied to partial synthesis of naturally occurring antitumor alkaloids of Catharanthus roseus. The circular dichroism technique is of high diagnostic value for this series of compounds to distinguish between the natural or unnatural C(16'') configurations. Another type of skeletal fragmentation at C(5)-C(6), also encountered during this study, was minimized under the experimental conditions.