TOTAL SYNTHESIS OF DL-ATISINE
TOTAL SYNTHESIS OF DL-ATISINE
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DOI：
10.1021/ja00982a036
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发表时间：
1967-01-01
影响因子：
15
通讯作者：
HAYASE, Y
中科院分区：
文献类型：
--
作者：
NAGATA, W;SUGASAWA, T;HAYASE, Y
首次全合成了外消旋体阿替辛。具有生物碱基本骨架的五环化合物42 c的合成是以立体化学明确和高度选择性的方式从三环共轭酮2开始实现的，这意味着所提出的阿替辛骨架的构型是合成证实的。利用烷基铝和氰化氢的氢氰化反应成功地建立了AE和CD桥环体系。五环化合物通过三步反应序列进一步转化为最终化合物46，其与天然系列中Pelletier的六步部分合成相连接，以完成阿替辛的全合成。
The first total synthesis of atisine in a racemic form is described. The synthesis of the pentacyclic compound 42c having the fundamental skeleton of the alkaloid was achieved in a stereochemically unequivocal and highly selective manner starting from the tricyclic conjugated ketone 2, implying that the suggested configuration of the atisine skeleton is substantiated synthetically. The new hydrocyanation reaction using alkylaluminum and hydrogen cyanide was successfully applied for building up both the AE and CD bridged ring system. The pentacyclic compound was further transformed by a three-step reaction sequence to the final compound 46, which is connected with the six-step, partial synthesis of Pelletier in the natural series to complete the total synthesis of atisine.