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Rapid Construction of Tetralin, Chromane, and Indane Motifs via Cyclative C−H/C−H Coupling: Four-Step Total Synthesis of (±)-Russujaponol F

preprint
submitted on 18.11.2020, 02:54 and posted on 18.11.2020, 12:52 by Zhe Zhuang, Alastair Herron, Shuang Liu, jin-quan yu
The development of practical C−H/C−H coupling reactions remains a challenging yet appealing synthetic venture because it circumvents the need to prefunctionalize both coupling partners for the generation of C−C bonds. Herein, we report a cyclative C(sp3)−H/C(sp2)−H coupling reaction of free aliphatic acids enabled by a cyclopentane-based mono-N-protected β-amino acid ligand. This reaction uses inexpensive sodium percarbonate (Na2CO3·1.5H2O2) as the sole oxidant, generating water as the only byproduct. A range of biologically important scaffolds, including tetralins, chromanes, and indanes, could be easily prepared by this protocol. Finally, the synthetic application of this methodology is demonstrated by the concise total synthesis of (±)-russujaponol F in a four-step sequence starting from readily available phenylacetic acid and pivalic acid through the sequential functionalizations of four C−H bonds.

Funding

NIH (NIGMS, R01GM084019)

NSF under the CCI Center for Selective C−H Functionalization (CHE-1700982)

The Scripps Research Institute

History

Email Address of Submitting Author

zhuang@scripps.edu

Institution

The Scripps Research Institute

Country

United States

ORCID For Submitting Author

0000-0001-6679-0496

Declaration of Conflict of Interest

no conflict of interest

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