College of Life Sciences, Beijing Normal University, Beijing, 100875, China.
National Institute of Biological Sciences (NIBS), Beijing, 102206, China.
Angew Chem Int Ed Engl. 2019 Apr 1;58(15):4988-4991. doi: 10.1002/anie.201900156. Epub 2019 Mar 6.
A reaction cascade of aza-Achmatowicz rearrangement followed by indole nucleophilic cyclization was developed to generate the common indole-fused azabicyclo[3.3.1]nonane core of the macroline family alkaloids. The key to the success of the strategy relies on the careful manipulation of protecting groups and judicious selection of chemoselective furan oxidation conditions. The synthetic utility was further demonstrated on the asymmetric total synthesis of (-)-alstofolinine A.
发展了aza-Achmatowicz 重排反应级联反应，然后进行吲哚亲核环化，生成了大环林家族生物碱的常见吲哚稠合氮杂双环[3.3.1]壬烷核心。该策略的成功关键在于仔细控制保护基团和明智选择选择性呋喃氧化条件。该合成方法的实用性进一步通过(-)-alstofolinine A 的不对称全合成得到了证明。
