4.8 Article

A Three-Step Process to Facilitate the Enantioselective Assembly of Cis-Fused Octahydrophenanthrenes with a Quaternary Stereocenter

Journal

ORGANIC LETTERS
Volume 24, Issue 14, Pages 2590-2595

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c00451

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Funding

  1. National Natural Science Foundation of China [21871152, 92056105, 21790332]
  2. National Key R&D Program of China [2021YFA1500200]
  3. Haihe Laboratory of Sustainable Chemical Transformations
  4. Frontiers Sciences Center for New Organic Matter (Nankai University) [63181206]

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This study reports a concise and efficient synthetic strategy for the rapid assembly of cis-fused octahydrophenanthrene scaffolds, resulting in the construction of compounds with an arylated all-carbon quaternary stereocenter.
A three-step process for the enantioselectiveassembly ofcis-fused octahydrophenanthrenes with a quaternarystereocenter is reported. This synthetic strategy relies on aregioselective gamma-alkylation, a one-pot sequence of asymmetrichydrogenation and oxidation, and an intramolecular enolatearylation to facilitate the rapid and enantioselective constructionofcis-fused octahydrophenanthrene scaffolds with an arylated all-carbon quaternary stereocenter concisely and efficiently.

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