Total synthesis of (+)-lithospermic acid by asymmetric intramolecular alkylation via catalytic C-H bond activation
Total synthesis of (+)-lithospermic acid by asymmetric intramolecular alkylation via catalytic C-H bond activation
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DOI：
10.1021/ja052680h
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发表时间：
2005-10-05
影响因子：
15
通讯作者：
Ellman, JA
中科院分区：
文献类型：
--
作者：
O'Malley, SJ;Tan, KL;Ellman, JA
报道了（+）-紫草酸的全合成。高效合成的特点是通过C-H键活化的不对称烷基化来组装天然产物的二氢苯并呋喃核心。这是通过手性亚胺导向的C-H键官能化完成的，代表了这种C-H活化方法在天然产物合成中的首次应用。此外，一个具有挑战性的脱保护的后期全甲基化的紫草酸实现。
The total synthesis of (+)-lithospermic acid is described. The efficient synthesis features an asymmetric alkylation via C−H bond activation to assemble the dihydrobenzofuran core of the natural product. This was accomplished via a chiral imine-directed C−H bond functionalization and represents the first application of this C−H activation method to natural product synthesis. Furthermore, a challenging deprotection of a late-stage permethylated lithospermic acid was achieved.