77034-26-5Relevant academic research and scientific papers
A three-step synthesis of the guaianolide ring system
Hullaert, Jan,Laplace, Duchan R.,Winne, Johan M.
supporting information, p. 3097 - 3100 (2014/06/09)
By using a gallium(III) triflate catalyzed intramolecular (4+3) cycloaddition, a few functionalized furan-derived tricycles that share the common guaianolide sesquiterpene ring system were prepared in a stereoselective manner in only three steps from commercially available starting materials. A discussion of the formation of alternative products is included, with possible substrate requirements to achieve the key cycloaddition step in an efficient way. Copyright
Divergent reaction pathways of a cationic intermediate: Rearrangement and cyclization of 2-substituted furyl and benzofuryl enones catalyzed by iridium(III)
Vaidya, Tulaza,Manbeck, Gerald F.,Chen, Sylvia,Frontier, Alison J.,Eisenberg, Richard
supporting information; experimental part, p. 3300 - 3303 (2011/05/04)
In contrast to 2-substituted pyrrole enones, furyl and benzofuryl enones do not undergo the Nazarov electrocyclization. Instead, these furyl and benzofuryl enones exhibit unusual rearrangement sequences in the presence of catalytic amounts of [IrBr(CO)(DIM)((R)-(+)-BINAP)](SbF6)2 (1; DIM = diethylisopropylidene malonate) and AgSbF6 (1:1). A 1,2-H shift followed by intramolecular Friedel-Crafts alkylation leads to synthetically valuable cyclohexanones with furanylic quaternary centers. The electrophilicity of 1 is essential for this rearrangement.
Asymmetric hydrogenation of furan-containing ketones over tartaric acid-modified Raney nickel catalyst
Haruna, Noriko,Acosta, Delicia E.,Nakagawa, Satoshi,Yamaguchi, Kohei,Tai, Akira,Okuyama, Tadashi,Sugimura, Takashi
, p. 375 - 386 (2007/10/03)
The hydrogenation of β-keto esters containing a furan unit at the conjugated position to the β-carbonyl group was carried out over a chiral heterogeneous catalyst, tartaric acid-modified Raney nickel. The hydrogenation first proceeds at the carbonyl to give optically active alcohols, but a simple substrate undergoes further hydrogenation of the furan part to produce a diastereomeric mixture of alcohols having a tetrahydrofuran moiety. This over-reduction was efficiently suppressed by substitutions of a substituent at the furan part. The optical yield at the hydroxy group is in the range of 40-90%.
