Total Synthesis of the Sesquiterpenoid Periconianone A Based on a Postulated Biogenesis : JACS 2017

Total Synthesis of the Sesquiterpenoid Periconianone A Based on a Postulated Biogenesis

The first enantioselective total synthesis of the complex tricarbocyclic sesquiterpenoid periconianone A based on a postulated biogenesis is reported. Key elements of the synthetic route include the use of an isopropenyl group as a removable directing group for stereoselective synthesis, a sequence featuring a Rh-mediated O–H insertion/[3,3]-sigmatropic rearrangement and subsequent α-ketol rearrangement, and a late stage aldol reaction to furnish the complex cage-like framework.

Article: DOI: 10.1021/jacs.7b10053

Total Synthesis of Paralemnolide A: Organic Letters 2017

Total Synthesis of Paralemnolide A

The first total synthesis of tricyclic bisnorsesquiterpene paralemnolide A, isolated from the soft coral Paralemnalia thyrsoides, was achieved. This synthesis features the lactonization of the cyclohexene derivative having a tert-butyl ester via stereoselective epoxidation followed by treatment with a Brønsted acid and construction of the novel tricyclic skeleton by an intramolecular Reformatsky–Honda reaction.