Enantioselective syntheses of aeruginosin 298-A and its analogues using a catalytic asymmetric phase-transfer reaction and epoxidation

Enantioselective syntheses of aeruginosin 298-A and its analogues using a catalytic asymmetric phase-transfer reaction and epoxidation
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DOI:
10.1021/ja037290e
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发表时间:
2003-09-17
影响因子:
15
通讯作者:
Shibasaki, M
Shibasaki, M
中科院分区:
化学1区
文献类型:
--
作者:
Ohshima, T;Gnanadesikan, V;Shibasaki, M

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我们开发了一种通用的合成方法,aerodosin 298-A以及几个有吸引力的类似物,其中所有的立体中心是通过催化不对称相转移反应和环氧化反应控制的。此外,激烈的抗衡阴离子的影响,在相转移催化首次观察到,使得有可能三维微调的催化剂(缩酮部分,芳香族部分,和抗衡阴离子)。
We developed a versatile synthetic process for aeruginosin 298-A as well as several attractive analogues, in which all stereocenters were controlled by a catalytic asymmetric phase-transfer reaction and epoxidation. Furthermore, drastic counteranion effects in phase-transfer catalysis were observed for the first time, making it possible to three-dimensionally fine-tune the catalyst (ketal part, aromatic part, and counteranion).