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Total Syntheses of Scabrolide A and Yonarolide

2023; American Chemical Society; Volume: 145; Issue: 16 Linguagem: Inglês

10.1021/jacs.3c02317

1943-2984

Roberto Serrano, Yaroslav D. Boyko, Lucas W. Hernandez, Aleksandras Lotuzas, David Šarlah,

Plant-derived Lignans Synthesis and Bioactivity

The concise total syntheses of oxidized norcembranoid terpenoids (−)-scabrolide A and (−)-yonarolide have been accomplished in 10 and 11 steps, respectively. The carbocyclic skeleton was efficiently constructed from two chiral-pool-derived fragments, including a [5,5]-bicyclic lactone accessed through a powerful Ni-catalyzed pentannulation of functionalized cyclopentenone with methylenecyclopropane and subsequent fragmentation. Additional features included a Liebeskind–Srogl coupling, induction of a cyclization/elimination cascade by a zinc-amido base, and installation of a sensitive enedione motif by late-stage γ-oxidation.