(-)-Lytophilippine A: synthesis of a C1-C18 building block.
(-)-Lytophilippine A: synthesis of a C1-C18 building block.
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(-)-Lytophilippine A：C1-C18 结构单元的合成。
DOI：
10.1021/ol1023008
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发表时间：
2010
期刊：
影响因子：
5.2
通讯作者：
M. Hiersemann
中科院分区：
文献类型：
--
作者：
Annika Gille;M. Hiersemann
实现了全合成（-）-lytophilippine A的保护的C1-C18结构单元的会聚对映选择性合成。催化的不对称Gosteli-Claisen重排和Evans羟醛缩合反应是C1-C7亚基组装过程中的关键C/C连接转化（从4步到10步，29%）。利用d-半乳糖作为廉价的非手性池起始材料（15步，15%）实现C8-C18片段的合成。合并的亚基是通过一个非常有效的序列，包括酯化和闭环复分解（五个步骤，56%）。
The convergent enantioselective synthesis of a protected C1-C18 building block for the total synthesis of (-)-lytophilippine A was achieved. A catalytic asymmetric Gosteli-Claisen rearrangement and an Evans aldol reaction served as key C/C-connecting transformations during the assembling of the C1-C7 subunit (10 steps from 4, 29%). The synthesis of the C8-C18 segment was achieved utilizing d-galactose as inexpensive ex-chiral-pool starting material (15 steps, 15%). The merger of the subunits was accomplished by a remarkably efficient sequence consisting of esterification and ring-closing metathesis (five steps, 56%).