Zhang Jie, Yu Longhui, Ogawa Hiroshige, Nagata Yuuya, Nakamura Hugh
The Hong Kong University of Science and Technology (HKUST), Clear Water Bay, 999077, Hong Kong SAR, China.
WPI Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Sapporo, 001-0021, Japan.
Angew Chem Int Ed Engl. 2024 Oct 14;63(42):e202409987. doi: 10.1002/anie.202409987. Epub 2024 Sep 12.
We report the development of a novel synthetic approach for the highly strained atrop-Tyr C-6-to-Trp N-1' linkage, which can be executed on a decagram scale using a modular strategy involving palladium-catalyzed C-H arylation followed by Larock macrocyclization. The first total synthesis of lapparbin (1) was achieved by applying this synthetic strategy. Furthermore, the modular synthesis utilizing C-H arylation and Larock macrocyclization, discovered in the total synthesis of lapparbin (1), was demonstrated to be applicable to various arbitrary biaryl linkages, including non-natural types.
我们报道了一种用于构建高张力的阿托-酪氨酸C-6至色氨酸N-1'连接的新型合成方法，该方法可采用模块化策略在十克规模上进行，包括钯催化的C-H芳基化反应，随后进行拉罗克大环化反应。通过应用该合成策略，首次实现了拉帕宾（1）的全合成。此外，在拉帕宾（1）全合成中发现的利用C-H芳基化和拉罗克大环化的模块化合成方法，被证明适用于各种任意的联芳基连接，包括非天然类型。
