253284-51-4Relevant academic research and scientific papers
Unified Approach to Furan Natural Products via Phosphine-Palladium Catalysis
Chen, Violet Yijang,Kwon, Ohyun
, 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.
Tandem Suzuki-Miyaura coupling/acid-catalyzed cyclization between vinyl ether boronates and vinyl halides: A concise approach to polysubstituted furans
Butkevich, Alexey N.,Meerpoel, Lieven,Stansfield, Ian,Angibaud, Patrick,Corbu, Andrei,Cossy, Janine
supporting information, p. 3840 - 3843 (2013/09/02)
Polysubstituted 2-(ω-hydroxyalkyl)furans were prepared by tandem Suzuki-Miyaura coupling/acid-catalyzed cyclization starting from appropriately substituted 3-haloallylic alcohols and dihydrofuran-, dihydropyran- or glycal-derived pinacol boronates.
Rhodium-catalyzed vinylcyclopropanation/cyelopentenation of strained alkenes via a sequential carborhodation process
Tseng, Nai-Wen,Lautens, Mark
supporting information; experimental part, p. 2521 - 2526 (2009/08/07)
A rhodium-catalyzed reaction of dienylboronate esters with alkenes is described. Strained bicyclic alkenes show the highest reactivity toward the rhodium-catalyzed addition of the dienylboronate esters. Depending on the substitution pattern of dienylboron
Synthesis of isocoumarins and α-pyrones via palladium-catalyzed annulation of internal alkynes
Larock, Richard C.,Doty, Mark J.,Han, Xiaojun
, p. 8770 - 8779 (2007/10/03)
A number of 3,4-disubstituted isocoumarins and polysubstituted α- pyrones have been prepared in good yields by treating halogen- or triflate- containing aromatic and α,β-unsaturated esters, respectively, with internal alkynes in the presence of a palladiu
