Enantioselective Total Synthesis of Andrographolide and 14‐Hydroxy‐Colladonin: Carbonyl Reductive Coupling and <i>trans</i>‐Decalin Formation by Hydrogen Transfer
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- Lin Yang
- University of Texas at Austin Department of Chemistry 105 E 24th Street (A5300) Austin TX 78712-1167 USA
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- Thomas Wurm
- University of Texas at Austin Department of Chemistry 105 E 24th Street (A5300) Austin TX 78712-1167 USA
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- Binit Sharma Poudel
- University of Texas at Austin Department of Chemistry 105 E 24th Street (A5300) Austin TX 78712-1167 USA
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- Michael J. Krische
- University of Texas at Austin Department of Chemistry 105 E 24th Street (A5300) Austin TX 78712-1167 USA
説明
<jats:title>Abstract</jats:title><jats:p>An enantioselective total synthesis of the labdane diterpene andrographolide, the bitter principle of the herb Andrographis paniculata (known as “King of Bitters”), was accomplished in 14 steps (LLS). Key transformations include iridium‐catalyzed carbonyl reductive coupling to form the quaternary C4 stereocenter, diastereoselective alkene reduction to establish the <jats:italic>trans</jats:italic>‐decalin ring, and carbonylative lactonization to install the α‐alkylidene‐β‐hydroxy‐γ‐butyrolactone.</jats:p>
収録刊行物
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- Angewandte Chemie International Edition
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Angewandte Chemie International Edition 59 (51), 23169-23173, 2020-10-15
Wiley