Jeon Jiye, Lee Sang Eun, Cheon Cheol-Hong
Department of Chemistry, Korea University, 145 Anam-ro, Seongbuk-gu, Seoul 02841, Republic of Korea.
Org Lett. 2021 Mar 19;23(6):2169-2173. doi: 10.1021/acs.orglett.1c00323. Epub 2021 Feb 25.
The total synthesis of (±)-hinckdentine A is described herein. A cyanide-catalyzed imino-Stetter reaction of the aldimine derived from ethyl 2-amino-3,5-dibromocinnamate and 5-bromo-2-nitrobenzaldehyde followed by oxidative rearrangement afforded a 2,2-disubstituted 3-indolinone derivative containing the carbon skeleton and all of the functional groups present in the natural product correctly positioned, including three bromine atoms. Subsequent D-ring formation and seven-membered C-ring construction completed the total synthesis of hinckdentine A.
本文描述了（±）-欣克登汀A的全合成。由2-氨基-3,5-二溴肉桂酸乙酯和5-溴-2-硝基苯甲醛衍生的醛亚胺进行氰化物催化的亚氨基-施泰特反应，随后进行氧化重排，得到了一种2,2-二取代的3-吲哚酮衍生物，其含有天然产物中存在的碳骨架和所有官能团，且位置正确，包括三个溴原子。随后形成D环和构建七元C环完成了欣克登汀A的全合成。
