4.8 Article

Total Synthesis of (±)-Lysergic Acid, Lysergol, and Isolysergol by Palladium-Catalyzed Domino Cyclization of Amino Allenes Bearing a Bromoindolyl Group

Journal

ORGANIC LETTERS
Volume 10, Issue 22, Pages 5239-5242

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol8022648

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Funding

  1. Ministry of Education, Culture, Sports, Science and Technology of Japan
  2. Targeted Proteins Research Program
  3. Japan Society for the Promotion of Science (JSPS) for Young Scientists

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Ergot alkaloids and their synthetic analogs have been reported to exhibit broad biological activity. We investigated direct construction of the C/D ring system of ergot alkaloids based on palladium-catalyzed domino cyclization of amino allenes. With this biscyclization as the key step, total synthesis of (+/-)-Iysergic acid, (+/-)-Iysergol, and (+/-)-isolysergol was achieved.

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