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An Oxidative Dearomatization Approach To Prepare the Pentacyclic Core of Ryanodol
journal contribution
posted on 2018-06-13, 13:55 authored by Chen Xu, Arthur Han, Sarah E. ReismanAn approach to synthesize the pentacyclic
framework of the polyol
diterpenoid ryanodol is reported. The ABC tricycle was constructed
by a Co-mediated Pauson–Khand reaction, and both radical and
anionic cyclization pathways were developed to form the E-ring. In
addition, a reaction sequence involving SeO2-mediated enone
oxidation and hydroxyl-directed oxy-Michael addition was developed
to introduce the A-ring oxidation. The feasibility of forming the
bridging D-ring by an oxidative dearomatization was established.
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D-ringPreparefeasibilityA-ring oxidationABC tricyclereaction sequencecyclization pathwaysSeO 2Oxidative Dearomatization Approachoxidative dearomatizationCo-mediatedpentacyclic frameworkpolyol diterpenoid ryanodolPausonE-ringenone oxidationRyanodolapproachPentacyclic Corehydroxyl-directed oxy-Michael addition
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