Organic Letters
Letter
the foundation for a scalable, convergent approach was
realized, assembling the carbon skeleton and seven stereo-
centers of jervine using simple reagents and practical, catalytic
sources of chirality (D-proline, L-proline, and Pseudomonas
fluorescens lipase). This route provides every carbon needed for
the target structure except for the D-ring methyl group, and it
is highlighted by the use of robust Ireland−Claisen and
selenoetherification reactions in order to stereoselectively
assemble a fully substituted spiro-tetrahydrofuran ring.
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ASSOCIATED CONTENT
* Supporting Information
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sı
The Supporting Information is available free of charge at
Experimental procedures, analytical data for new
compounds, and NMR spectra (PDF)
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Accession Codes
CCDC 1986262 (29) contains the supplementary crystallo-
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AUTHOR INFORMATION
Corresponding Author
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Jeffrey S. Johnson − Department of Chemistry, University of
North Carolina at Chapel Hill, Chapel Hill, North Carolina
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Authors
Blane P. Zavesky − Department of Chemistry, University of
North Carolina at Chapel Hill, Chapel Hill, North Carolina
27599-3290, United States
Pedro De Jesus Cruz − Department of Chemistry, University of
North Carolina at Chapel Hill, Chapel Hill, North Carolina
27599-3290, United States
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Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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The project described was supported by Award No. R35
GM118055 from the National Institute of General Medical
Sciences, and P.D.J.C. acknowledges support through a
supplement to this grant. We thank the UNC Dept. of
Chemistry Mass Spectrometry Core laboratory, especially Dr.
B. Ehrmann, for assistance with mass spectrometry analysis on
instrumentation acquired through the NSF MRI program
under Award No. CHE-1726291 and a supplement to
GM118055. We thank the UNC Dept. of Chemistry NMR
Core Laboratory, especially Dr. M. ter Horst, for assistance
with NMR analysis on instrumentation acquired through the
NSF MRI program under Award No. CHE-1828183. We
thank Dr. C.-H. Chen for assistance with X-ray crystallography
experiments. We thank Dr. M. Horwitz and J. Robins of these
laboratories (UNC) for useful discussions.
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D
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