An asymmetric catalytic multi-component reaction enabled the green synthesis of isoserine derivatives and semi-synthesis of paclitaxel  

作　　者：Taoda Shi Xinglin Li Yukai Li Xiang Fu Linna Wu Dengqing Wu Wenhao Hu 

机构地区：[1]Guangdong Chiral Drug Engineering Laboratory,School of Pharmaceutical Sciences,Sun Yat-sen University,Guangzhou 510000,China

出　　处：《Green Synthesis and Catalysis》2023年第1期58-63,共6页绿色合成与催化（英文）

基　　金：Support for this research from the National Natural Science Foundation of China(Nos.92056201 and 82003592);Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery(No.2019B030301005);The Program for Guangdong Introducing Innovative and Entrepreneurial Teams(No.2016ZT06Y337)and Zhujiang Talent Program Postdoctoral Funding Project is greatly acknowledged。

摘　　要：Paclitaxel(Taxol^(@))as a cornerstone of chemotherapy remains in high demand.The semi-synthesis of paclitaxel via coupling of Taxus leaf-produced baccatin III and manually synthesized isoserine(C-13 side chain)is one of the solutions to avoid environmental damage caused by the sacrifice of the whole Taxus brevifolia.A green synthesis of the C-13 side chain is pivotal to the green production of paclitaxel.We herein report a green synthesis of isoserine derivatives and the semi-synthesis of paclitaxel via a straightforward assembly of isoserines based on an Rh2(TPA)3(OAc)/CPA1 co-catalyzed asymmetric multi-component reaction of ethyl diazoacetate,triethyl silanol and N-(anthrancen-9-ylmethyl)benzaldimine.The method is featured by improved atom economy,effective mass yield,and environmental factors compared to our previous racemic method and BMS company's semi-synthesis method.And the method allows for rapid access to paclitaxel derivatives with varied C-13 side chains.

关 键 词：Asymmetric catalysis Multi-component reaction Green semi-synthesis PACLITAXEL 

分 类 号：O643.36[理学—物理化学]