State Key Laboratory of Phytochemistry and Plant Resources in West China , Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201 , China.
University of Chinese Academy of Sciences , Beijing 100049 , China.
Org Lett. 2018 Aug 3;20(15):4575-4578. doi: 10.1021/acs.orglett.8b01861. Epub 2018 Jul 13.
A synthetic strategy for the catalytic asymmetric total synthesis of (-)-actinophyllic acid is described. This highly efficient and enantioselective approach allows the rapid installation of the four contiguous chiral centers (C16, C15, C20, and C19) by way of a dual Ir/amine catalytic allylation of 2-indolyl vinyl carbinol 6 and an aldol reaction of resultant chiral aldehyde 4a with 2-pyrrolidinone 5. The key indol-3-ylmethanamine moiety and 1-azabicyclo[4.2.1]nonane ring system were readily generated through a selective Mannich-like cyclization and an intramolecular N-alkylation, respectively.
描述了一种用于催化不对称全合成（-）-actinophyllic 酸的合成策略。这种高效和对映选择性的方法可以通过 2-吲哚基乙烯基甲醇 6 的双 Ir/胺催化烯丙基化反应和手性醛 4a 与 2-吡咯烷酮 5 的醛醇反应，快速构建四个连续手性中心（C16、C15、C20 和 C19）。关键的吲哚-3-基甲胺部分和 1-氮杂双环[4.2.1]壬烷环系统可以通过选择性的 Mannich 型环化和分子内 N-烷基化分别容易地生成。
