An Oxidative Dearomatization Approach To Prepare the
Pentacyclic Core of Ryanodol
Posted on 2018-06-13 - 13:55
An 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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Xu, Chen; Han, Arthur; Reisman, Sarah E. (2018). An Oxidative Dearomatization Approach To Prepare the
Pentacyclic Core of Ryanodol. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.8b01387
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AUTHORS (3)
CX
Chen Xu
AH
Arthur Han
SR
Sarah E. Reisman
KEYWORDS
D-ringPreparefeasibilityA-ring oxidationABC tricyclereaction sequencecyclization pathwaysSeO 2Oxidative Dearomatization Approachoxidative dearomatizationCo-mediatedpentacyclic frameworkpolyol diterpenoid ryanodolPausonE-ringenone oxidationRyanodolapproachPentacyclic Corehydroxyl-directed oxy-Michael addition