Model Studies to Access the [6,7,5,5]-Core of Ineleganolide Using Tandem Translactonization-Cope or Cyclopropanation-Cope Rearrangements as Key Steps
Recently, we reported a convergent cyclopropanation–Cope approach to the core of ineleganolide, which was the first disclosed synthesis of the core of the norditerpene natural product ineleganolide. In this complementary work, a model system for the core of ineleganolide has been prepared through a series of tandem cyclopropanation–Cope and translactonization–Cope rearrangements. Work with this model system has enriched our understanding of the cyclopropanation–Cope rearrangement sequence. Additionally, research into this model system has driven the development of tandem translactonization–Cope rearrangements.
Additional Information© 2017 American Chemical Society. Received: August 11, 2017; Published: November 7, 2017. The authors wish to thank the NIH-NIGMS (R01GM080269), Amgen, the Gordon and Betty Moore Foundation, and Caltech for financial support. Additionally, the authors gratefully acknowledge Larry Henling and the late Dr. Michael Day (Caltech) for X-ray crystallographic structural determination; Dr. Mona Shahgholi and Naseem Torian (Caltech) for mass spectrometric analysis; Dr. David VanderVelde (Caltech) for NMR experimental assistance and helpful discussions; Dr. Masaki Seto, Dr. N. Sherden, and Dr. D. E. White for helpful discussions; and Dr. R. A. Craig, II for editorial suggestions. J.L.R. thanks the California Tobacco-Related Disease Research Program of the University of California, Grant Number 14DT-0004 for a predoctoral fellowship. A.C.J. thanks the NIH (F32GM082000) for a postdoctoral fellowship. The authors declare no competing financial interest.
Accepted Version - nihms918699.pdf
Supplemental Material - jo7b02030_si_001.pdf
Supplemental Material - jo7b02030_si_002.cif