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 (−)-Geissoschizol through Ir-Catalyzed Allylic Amidation as the Key Step: OL 2017

Total Synthesis of (−)-Geissoschizol through Ir-Catalyzed Allylic Amidation as the Key Step

The iridium-catalyzed, Zn(OTf)2 promoted asymmetric allylic amidation of a secondary alcohol derived from tryptamine has been utilized to forge a tetrahydro-β-carboline. Based on this key step, a novel, facile, and enantioselective total synthesis of (−)-geissoschizol was achieved in 10 steps.

More Information: http://pubs.acs.org/doi/10.1021/acs.orglett.7b03133