A Bismuth(III)-Catalyzed Friedel-Crafts Cyclization and Stereocontrolled Organocatalytic Approach to (-)-Platensimycin
A Bismuth(III)-Catalyzed Friedel-Crafts Cyclization and Stereocontrolled Organocatalytic Approach to (-)-Platensimycin
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DOI：
10.1021/ol102390t
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发表时间：
2010-12-03
期刊：
影响因子：
5.2
通讯作者：
Lear, Martin J.
中科院分区：
文献类型：
--
作者：
Eey, Stanley T. -C.;Lear, Martin J.
介绍了一条高产的（-）-铂霉素核心的合成路线。这需要发现Bi（OTf）（3）催化游离内半缩醛的傅-克环化反应，并辅以LiClO 4抑制磺酸盐基团的刘易斯碱性。TBAF-促进环脱芳构化后，通过采用基于胺的有机催化原理来逆转底物的固有空间控制，实现了二烯酮的非对映选择性共轭还原。
A high yielding route to the (-)-platensimycin core is communicated. This entailed the discovery of Bi(OTf)(3) to catalyze a Friedel-Crafts cyclization of a free lactol, supplemented by LiClO4 to suppress the Lewis basicity of the sulfonate group. After TBAF-promotecl cyclodearomatization, a diastereoselective conjugate reduction of a dienone was achieved by adopting amine-based organocatalytic rationales to reverse the inherent steric control of the substrate.