An oxidative Wagner-Meerwein transposition involving different functionalities mediated by a hypervalent iodine reagent has been accomplished. The strategy fits within the concept of "aromatic ring umpolung" and allows rapid access to highly functionalized cores.

No abstract

Treatment of various dienimides in the presence of a Lewis acid and (trimethylsiloxy)furan leads to the corresponding aniline furan‐2(5H)‐ones. The same treatment with furan yields a triaryl product and, surprisingly, a byproduct with a pentacyclo[5.4.0.0.0.0]undecane main core. The formation of this birdcage system containing nine stereogenic centres was produced with complete diastereoselectivity.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

No abstract

An unprecedented oxidative Prins transformation on phenol derivatives mediated by a hypervalent iodine reagent has been developed. This method allows a rapid access to highly substituted compact systems present in several natural products via a carbon-based addition on an aromatic core. Substitution at each ring position has been demonstrated, enabling synthesis of molecules with up to two contiguous quaternary carbon centers in good yield.