Palladium-Catalyzed α-Arylation of Cyclic Vinylogous Esters for the Synthesis of γ-Arylcyclohexenones and Total Synthesis of Aromatic Podocarpane Diterpenoids

Wen Yi Hou, Yen-Ku Wu*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

Described is a method for the formal γ-arylation of cyclohexenones allowing synthesis of a remote all-carbon quaternary center. The process involves the palladium-catalyzed α-arylation of a α-substituted cyclic vinylogous ester followed by the Stork-Danheiser transposition. The synthetic utility of this protocol is featured in the total syntheses of (±)-12-hydroxy-13-methylpodocarpa-8,11,13-trien-3-one, (±)-3β,12-dihydroxy-13-methylpodocarpane-8,11,13-triene, and (±)-O-methyl nimbinone.

Original languageEnglish
Pages (from-to)1220-1223
Number of pages4
JournalOrganic Letters
Volume19
Issue number5
DOIs
StatePublished - 3 Mar 2017

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