Studies on a cycloisomerization reaction of 2-prenylated-2H-pyrans towards cis-fused tetrahydro-6H-benzo[c]chromene systems (reduced cis-THC analogues) are reported. The transformation is catalyzed by iron chloride and proceeds with the formation of two new bonds and two stereocenters diastereoselectively. The same catalyst also promotes the formation...

The catalytic asymmetric synthesis of voriconazole, a synthetically challenging antifungal agent was achieved in nine steps with a 8 % overall yield. This novel strategy relied on the precise synthesis of tetrasubstituted (Z)-allylic alcohol and the subsequent highly efficient epoxidation to establish the critical contiguous carbon stereocenters in...

Glycal family offers an interesting platform whose reactivity let the possibility to reach diverse glycoanalogues. In particular, the Ferrier rearrangement allows the introduction of diverse nucleophiles on the anomeric position but stays limited with regard to the nitrogen-containing nucleophiles, which can be possibly used with success. Herein, we...

European Journal of Organic Chemistry, EarlyView.

Reliable protocols for synthesis of furan-3(2H)-ones were developed and the resulting heterocycles were coupled to elaborate aldehydes in aldol couplings and condensations in good to high selectivity. Application of these methods allowed for a concise and highly stereroselective synthesis of the C8-C22 fragment of the complex polyketide natural product...

Nitrile-stabilized quaternary ammonium ylide as an effective aryl-cyanomethylene transfer agent has been explored for the first time, which enables a spirocyclopropanation process with conjugated carboxamide of indole heterocycle. The developed In(OTf)3-catalyzed method provides a straightforward, diastereoselective access to pharmaceutically relevant...