A Selective Intramolecular 5-exo-dig or 6-endo-dig Cyclization en Route to 2-Furanone or 2-Pyrone Containing Tricyclic Scaffolds

A Selective Intramolecular 5-exo-dig or 6-endo-dig Cyclization en Route to 2-Furanone or 2-Pyrone Containing Tricyclic Scaffolds

Ringfused bicyclic 2-pyridones exhibit interesting biological properties against pili assembly in uropathogenic Escherichia coli (Pinkner, J. S. et al. Proc. Natl. Acad. Sci. U. S. A.2006, 103, 17897-17902; Åberg, V. et al. Org. Biomol. Chem.2007, 5, 1827-1834) as well as curli formation (Cegelski, L. et al. Nat. Chem. Biol.2009, 5, 913-919). In the search for new ring-fused central fragments...

To dig or not to dig.

5-Exo-dig radical cyclization of enediynes: the first synthesis of tin-substituted benzofulvenes.

[reaction: see text] Bu(3)Sn-mediated 5-exo-dig radical cyclization of diaryl enediynes provides a mild and efficient approach to tin-substituted fulvenes. Further synthetic opportunities opened by this process and general factors responsible for the observed regio- and stereoselectivity are outlined.

The 5-exo-dig Cyclization of Bmdms Propargylic Ethers: an Efficient Trigger for Radical Cascades

This article reviews our contribution in the field of radical synthetic chemistry, focusing on cascades relying on the use of propargylic BMDMS ethers and asymmetric synthesis using enantiopure vinylsulfoxides. THE 5-EXO-DIG CYCLIZATION OF BMDMS PROPARGYLIC ETHERS: AN EFFICIENT TRIGGER FOR RADICAL CASCADES The vinyl radical, a precious tool The vinyl radical of type 3 resulting from the highly ...

[3,3]-Sigmatropic rearrangement/5-exo-dig cyclization reactions of benzyl alkynyl ethers: synthesis of substituted 2-indanones and indenes.

Substituted benzyl alkynyl ethers, prepared from the corresponding α-alkoxy ketones in a two-step sequence involving enol triflate formation and KOtBu-induced E2 elimination, undergo [3,3]-sigmatropic rearrangement/intramolecular 5-exo-dig cyclization at 60 °C to form substituted 2-indanones in good overall yields. 1,3-cis-Disubstituted-2-indanones are formed preferentially when the benzylic su...