253284-33-2Relevant academic research and scientific papers
Efficient Synthesis of Polysubstituted Furans through a Base-Promoted Oxacyclization of (Z)-2-En-4-yn-1-ols
Hrizi, Asma,Thiery, Emilie,Romdhani-Younes, Moufida,Jacquemin, Johan,Thibonnet, Jér?me
supporting information, p. 3798 - 3806 (2021/06/14)
An efficient base catalyzed oxacyclization of Z-enynols has been developed under transition metal-free reaction conditions, thus resulting in a variety of new di-, tri-, and tetra-substituted furans. This approach allowed us to obtain 32 new compounds. Furthermore, DFT calculations were realized to depict a relationship between the natural population analysis and experimental results with alkyl or aryl groups for the synthesis of 2-benzylfuran. A one-pot Sonogashira/oxacyclization approach offers a flexible, robust and efficient alternative to base catalyzed cyclization is also carried out.
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.
Generation of medium-ring cycloalkynes by ring expansion of vinylogous acyl triflates
Tummatorn, Jumreang,Dudley, Gregory B.
supporting information; experimental part, p. 1572 - 1575 (2011/04/26)
Reductive cyclization of aryl and vinyl iodides tethered to vinylogous acyl triflates (VATs) induces a ring-expanding fragmentation to provide cyclic alkynyl ketones, including strained nine-membered cycloalkynes, in fair to excellent yield. The tandem cy
Metal-catalyzed cycloisomerization of enyne functionalities via a 1,3-alkylidene migration
Lin, Ming-Yuan,Das, Arindam,Liu, Rai-Shung
, p. 9340 - 9341 (2007/10/03)
We report a new metal-catalyzed 6-endo-dig cyclization of cis-4,6-dien-1-yn-3-ols, which produces substituted benzene and naphthalene derivatives with structural reorganization. In this process, we observe a 1,3-alkylidene migration via cleavage of the olefin double bond of the starting substrates. The ease and reliability of this cyclization are manifested by its compatibility with a wide array of diverse substrates and several π-alkyne activators, including PtCl2, Zn(OTf)2, AuCl, and AuCl3. Copyright
Carbopalladation of nitriles: Synthesis of benzocyclic ketones and cyclopentenones via Pd-catalyzed cyclization of ω-(2-iodoaryl)alkanenitriles and related compounds
Pletnev, Alexandre A.,Larock, Richard C.
, p. 9428 - 9438 (2007/10/03)
An efficient procedure for the synthesis of 2,2-disubstituted benzocyclic ketones by intramolecular carbopalladation of nitriles has been developed. The cyclization of substituted 3-(2-iodoaryl)-propanenitriles affords indanones in high yields. The reaction is compatible with a wide variety of functional groups. This methodology has been extended to the synthesis of tetralones and cyclopentenones.
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
