Total Synthesis of Pactamycin and Pactamycate: A Detailed Account
Total Synthesis of Pactamycin and Pactamycate: A Detailed Account
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DOI：
10.1021/jo301638z
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发表时间：
2012-11-02
影响因子：
3.6
通讯作者：
Deschenes-Simard, Benoit
中科院分区：
文献类型：
--
作者：
Hanessian, Stephen;Vakiti, Ramkrishna Reddy;Deschenes-Simard, Benoit
本文描述了首次全合成巴塔霉素和巴塔霉素的合成研究，同时还完成了两种已知的同源物：脱 6-MSA-巴塔霉素 和脱 6-MSA-巴塔霉素（缺乏 6-甲基水杨基部分）。从 L-苏氨酸作为凯龙开始，一系列立体控制缩合产生了含有螺环恶唑啉的关键环戊烯酮。一系列系统的官能化最初导致不正确的环戊酮环氧化物，其在溶剂分解条件下被“反转”。其余基团的安装和恶唑啉的操作最终产生了巴他霉素、巴他霉素及其脱水杨基类似物。
This article describes synthetic studies that culminated in the first total synthesis of pactamycin and pactamycate and, in parallel, the two known congeners, de-6-MSA-pactamycin and de-6-MSA-pactamycate, lacking the 6-methylsalicylyl moiety. Starting with L-threonine as a chiron, a series of stereocontrolled condensations led to a key cyclopentenone harboring a spirocyclic oxazoline. A series of systematic functionalizations led initially to the incorrect cyclopentanone epoxide, which was "inverted" under solvolytic conditions. Installation of the remaining groups and manipulation of the oxazoline eventually led to pactamycin, pactamycate, and their desalicylyl analogues.