Two approaches to 14,15-secoergostane intermediates for the synthesis of strophasterols
Two approaches to 14,15-secoergostane intermediates for the synthesis of strophasterols
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合成 14,15-麦角甾烷中间体用于合成 stropasterols 的两种方法
DOI：
10.1080/09168451.2018.1452603
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发表时间：
2018
期刊：
影响因子：
--
通讯作者：
Shigefumi Kuwahara
中科院分区：
文献类型：
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作者：
Yuki Fukuda;Shuntaro Sato;Yusuke Ogura;Shigefumi Kuwahara
通过两种不同的途径合成了两种受保护的14,15-二角麦角烷衍生物，它们适合作为合成strophasterols A和B的关键中间体，抗mrsa和具有最近发现的strophastane骨架的神经细胞保护天然产物。第一种方法采用α-羟基酮中间体的氧化裂解，以Jones试剂为关键步骤，分十步从麦角甾醇中得到目标的二麦角甾醇。在第二种方法中，一个前所未有的由四个反应组成的反应级联使我们能够在六个步骤中更有效地获得二麦角斯坦。
Two protected 14,15-secoergostane derivatives suitable as pivotal intermediates for the synthesis of strophasterols A and B, anti-MRSA and neuronal cell-protecting natural products bearing a recently discovered strophastane skeleton, have been synthesized by two different routes. The first approach employed an oxidative cleavage of an α-hydroxy ketone intermediate with the Jones reagent as the key step to reach the targeted secoergostane from ergosterol in ten steps. In the second approach, an unprecedented reaction cascade composed of four reactions enabled us to obtain the secoergostane more efficiently in six steps.