4.8 Article

Total Synthesis of (-)-Lepenine

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 18, Pages 6598-6601

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja503023h

Keywords

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Funding

  1. JSPS KAKENHI [20002004, 25221301]
  2. Platform for Drug Discovery, Informatics, and Structural Life Science (MEXT)
  3. Mochida Memorial Foundation for Medical and Pharmaceutical Research
  4. Uehara Memorial Foundation
  5. JSPS
  6. Grants-in-Aid for Scientific Research [12J10970] Funding Source: KAKEN

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The first asymmetric total synthesis of lepenine has been accomplished. The synthesis features a tethered intramolecular Diels-Alder reaction, an intramolecular Mannich reaction, and a Diels-Alder reaction between an ortho-quinone monoketal and ethylene, resulting in stereoselective construction of the unique hexacyclic system.

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