@article{dfd2544026684a9dbf366f15cefc03a4,
title = "A Concise Synthesis of Pleurotin Enabled by a Nontraditional C-H Epimerization",
abstract = "An 8-step synthesis of a known pentacyclic intermediate toward the natural product pleurotin (1) is described. Pleurotin and related benzoquinone natural products are of great interest for their powerful anticancer and antibiotic activities. The route features a regio- and diastereoselective intermolecular photoenolization/Diels-Alder cycloaddition and an alkoxy-radical-induced hydrogen atom transfer-mediated C-H epimerization to construct pleurotin's carbon framework with appropriate relative stereochemical relationships. The synthesis concludes with a ring-forming benzylic C-H oxidation to deliver oxepane 19.",
author = "Hoskin, {John F.} and Sorensen, {Erik J.}",
note = "Funding Information: This research was supported by the National Science Foundation, CHE-2102663. We thank Drs. David Siler and David Ebner for early model system studies. We thank Dr. Philip Jeffrey for X-ray crystallographic analysis of compound 19 . We would like to thank Prof. Robert Knowles for helpful discussions and the MacMillan laboratory for use of their equipment. We also thank Johnny Wang (MacMillan lab) for assistance performing UV photoreactions and HPLC separations as well as for helpful discussions. Ben Hejna (Knowles Lab) is thanked for a donation of TRIP thiol. J.F.H. would like to thank the Ted Taylor Fellowship (Princeton) and the Bristol-Myers Squibb Graduate Fellowship in Synthetic Organic Chemistry for funding. Dr. Istv{\'a}n Pelczer, Kenith Conover, Dr. John Eng, and Dr. Sandra Knowles are acknowledged for analytical assistance. Publisher Copyright: {\textcopyright} 2022 American Chemical Society.",
year = "2022",
month = aug,
day = "10",
doi = "10.1021/jacs.2c06504",
language = "English (US)",
volume = "144",
pages = "14042--14046",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "31",
}