Laboratoire de Chimie Organique, ESPCI ParisTech, CNRS, 10 rue Vauquelin, 75231 Paris Cedex 05, France.
Org Lett. 2010 Sep 17;12(18):4074-7. doi: 10.1021/ol101659y.
The enantioselective total synthesis of the dual-specificity phosphatase inhibitor (-)-bitungolide F has been achieved using two convergent routes. Both strategies feature an asymmetric boron-mediated pentenylation, a stereoselective aldol, and a hydroxyl-directed 1,3-anti-reduction in order to control the stereogenic centers at C4, C5, C9, and C11. Whereas the first total synthesis was achieved in 11 steps and 14.6% overall yield using an Evans-type asymmetric alkylation, the second was completed in 9 steps and 11.4% overall yield using a highly enantioselective organocatalytic Michael addition as a key step and a protecting group free strategy.
已采用两条汇聚路线实现了双特异性磷酸酶抑制剂（-）-比通醇 F 的对映选择性全合成。这两种策略都采用了不对称硼介导的戊烯化、立体选择性的羟醛缩合以及羟基定向的 1,3-anti-还原反应，以控制 C4、C5、C9 和 C11 处的立体中心。第一个全合成是使用 Evans 型不对称烷基化反应以 11 步和 14.6%的总收率实现的，而第二个全合成是以高度对映选择性的有机催化迈克尔加成反应作为关键步骤和无保护基策略，以 9 步和 11.4%的总收率完成的。
