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 - Funding Information:
Financial support for this work was provided by the University of Illinois (Seemon H. Pines Graduate Fellowship to Y.B.), Bristol-Myers Squibb (predoctoral fellowship to Y.B.), and the National Science Foundation (CHE-2154393 and predoctoral fellowship to L.W.H.). We thank the SCS NMR Lab, Dr. D. Olson, and Dr. L. Zhu (University of Illinois) for technical support and NMR spectroscopic assistance. We also thank Alexander Shved, Dr. D. L. Gray, and Dr. T. Woods for X-ray crystallographic analysis assistance, and F. Sun for mass spectrometric assistance. We acknowledge Samantha Barlock and Peter Ryffel for critical proofreading of this paper.
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 -