Total synthesis of (±)-lysergic acid, lysergol, and isolysergol by palladium-catalyzed domino cyclization of amino allenes bearing a bromoindolyl group

Shinsuke Inuki, Shinya Oishi, Nobutaka Fujii, Hiroaki Ohno

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Abstract

(Chemical Equation Presented) 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 (±)-lysergic acid, (±)-lysergol, and (±)-isolysergol was achieved.

Original languageEnglish
Pages (from-to)5239-5242
Number of pages4
JournalOrganic Letters
Volume10
Issue number22
DOIs
Publication statusPublished - 2008 Dec 1

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ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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