13086-06-1Relevant articles and documents
Unified Approach to Furan Natural Products via Phosphine-Palladium Catalysis
Chen, Violet Yijang,Kwon, Ohyun
supporting information, p. 8874 - 8881 (2021/03/17)
Polyalkyl furans are widespread in nature, often performing important biological roles. Despite a plethora of methods for the synthesis of tetrasubstituted furans, the construction of tetraalkyl furans remains non-trivial. The prevalence of alkyl groups in bioactive furan natural products, combined with the desirable bioactivities of tetraalkyl furans, calls for a general synthetic protocol for polyalkyl furans. This paper describes a Michael–Heck approach, using sequential phosphine-palladium catalysis, for the preparation of various polyalkyl furans from readily available precursors. The versatility of this method is illustrated by the total syntheses of nine distinct polyalkylated furan natural products belonging to different classes, namely the furanoterpenes rosefuran, sesquirosefuran, and mikanifuran; the marine natural products plakorsins A, B, and D and plakorsin D methyl ester; and the furan fatty acids 3D5 and hydromumiamicin.
PPh3-catalyzed reactions of alkyl propiolates with N-tosylimines: A facile synthesis of alkyl 2-[aryl(tosylimino)methyl]acrylate and an insight into the reaction mechanism
Liu, Huimin,Zhang, Qiongmei,Wang, Limin,Tong, Xiaofeng
scheme or table, p. 1968 - 1972 (2010/06/19)
A new PPh3-catalyzed synthesis of alkyl 2-[aryl(tosylimino) methyl]acrylates from propiolate and N-tosylimine has been developed. Deuterium-labelling experiments show that the reaction mechanism involves several hydrogen-transfer processes, whi
