Visible-Light-Induced Intermolecular Dearomative Cyclization of Furans: Synthesis of 1-Oxaspiro[4.4]nona-3,6-dien-2-one
A fac-Ir(ppy)3-catalyzed intermolecular dearomative cyclization of 2-bromo-2-((5-bromofuran-2-yl)methyl)malonate and alkynes affording substituted spirolactones in yields of 19-91% via a 5-exo-dig radical cyclization under visible light is presented. This method provides a new access to the synthesis of spirocycle skeletons applying water as an external oxygen source under mild reaction conditions.
Bifunctional Furfuryl Cations Strategy: Three-Component Synthesis of Enamidyl Triazoles
A new multicomponent synthesis of functionalized enamidyl triazoles starting from simple and readily available starting materials is described. A simple treatment of a dichloromethane solution of an azide, amine, and 5-bromo-2-furylcarbinol with a Lewis acid provides the enamidyl triazole in good to high yield. A triple domino sequence, formal [3+2] cycloaddition/ring-opening/amidation, is involved in this new skeleton-generating reaction.
Application of furyl-stabilized sulfur ylides to a concise synthesis of 8a-epi-swainsonine
The total synthesis of 8a-epi-swainsonine has been achieved in 20% overall yield from R-glyceraldehyde dimethylacetonide 3 through epoxidation with the achiral furyl-substituted sulfonium ylide 2d as one of the key steps. The Royal Society of Chemistry.
Bi, Jie,Aggarwal, Varinder K.
p. 120 - 122
(2008/09/19)
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