TY - JOUR
T1 - Total Syntheses of Scabrolide A and Yonarolide
AU - Serrano, Roberto
AU - Boyko, Yaroslav D.
AU - Hernandez, Lucas W.
AU - Lotuzas, Aleksandras
AU - Sarlah, David
N1 - Publisher Copyright:
© 2023 American Chemical Society.
PY - 2023/4/26
Y1 - 2023/4/26
N2 - 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.
AB - 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.
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U2 - 10.1021/jacs.3c02317
DO - 10.1021/jacs.3c02317
M3 - Article
C2 - 37067516
AN - SCOPUS:85158053023
SN - 0002-7863
VL - 145
SP - 8805
EP - 8809
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 16
ER -