A practical enantioselective total synthesis of the bengamides B, E, and Z
A practical enantioselective total synthesis of the bengamides B, E, and Z
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DOI：
10.1021/ol026101e
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发表时间：
2002-06-13
期刊：
影响因子：
5.2
通讯作者：
Shook, BC
中科院分区：
文献类型：
--
作者：
Boeckman, RK;Clark, TJ;Shook, BC
[图]描述了从常见多元醇中间体合成 Bengamides B、E 和 Z 的实用全合成方法。连续的羟醛缩合提供了适合与 Bengamides 偶联的受保护的多元醇硫酯侧链。新型手性相转移催化的对映选择性烷基化提供了 Bengamides B 和 Z 所需的更高功能化的氨基己内酰胺。使用与对映选择性羟醛缩合所需的硼路易斯酸相容的 2-萘基甲基醚保护基团，可以直接获得 Bengamide B。
[GRAPHIC]A practical total synthesis of Bengamides B, E, and Z from a common polyol intermediate is described. Consecutive aldol condensations afford a protected polyol thioester side chain suitable for coupling to the Bengamides. A novel chiral phase transfer catalyzed enantioselective alkylation affords the more highly functionalized amino caprolactams required for Bengamides B and Z. Use of the 2-naphthylmethyl ether protecting group, compatible with the boron Lewis acids required for enantioselective aldol condensation, allows direct access to Bengamide B.