5460-70-8Relevant articles and documents
Scope and limitations of the double [4+3]-cycloadditions of 2-oxyallyl cations to 2,2′-methylenedifuran and derivatives
Meilert, Kai Torsten,Schwenter, Marc-Etienne,Shatz, Yuli,Dubbaka, Srinivas Reddy,Vogel, Pierre
, p. 2964 - 2967 (2003)
The reactivity of various 2-oxyallyl cations toward 2,2′-methylenedifuran (1b), 2,2′-(hydroxymethyl)-difuran (1c), 2,2′-(trimethylsilylmethylene)difuran (1d), and di(2-furyl)methanone (1e) has been explored. Difuryl derivatives 1c, 1d, and 1e refused to undergo formal double [4+3]-cycloadditions. Conditions have been found to convert 1b into meso-1,1′-methylenedi[(1R,1′S,5S,5′R)-(3) and (±)-1,1′-methylenedi[(1RS,1′SR,5SR,5′RS)- 8-oxabicyclo[3.2.1]oct-6-en-3-one] (4) that do not require CF3CH(OH)CF3 as solvent. High yields of meso-1,1′-methylenedi[(1R,1′S,2S,2′R,4R,4′S, 5S,5′R)- (5) and (±).1,1′-methylenedi[(1RS,1′RS,2SR,2′SR, 4RS,4′RS,5SR,5′SR)-2,4-dimethyl-8-oxabicyclo[3.2.1]oct-6- en-3-one] (6) have been obtained when 1b was reacted with 2,4-dibromopentan-3-one (7h) and NaI/Cu.
Synthesis of 2,5-dihydrofurans via alkylidene carbene insertion reactions
Walker, Louise F.,Connolly, Stephen,Wills, Martin
, p. 5273 - 5276 (2007/10/03)
The insertion of vinylidene carbenes into C-H bonds is an efficient method for the synthesis of 2,5-dihydrofurans. The methodology provides a convenient entry to the core structure of squalestatin/zaragozic acid natural products.