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

Research output: Contribution to journalArticle

64 Citations (Scopus)

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
Externally publishedYes

Fingerprint

Lysergic Acid
Bearings (structural)
Ergot Alkaloids
alkaloids
Cyclization
Palladium
palladium
acids
synthesis
activity (biology)
Bioactivity
analogs
rings
propadiene
lysergol

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Total synthesis of (±)-lysergic acid, lysergol, and isolysergol by palladium-catalyzed domino cyclization of amino allenes bearing a bromoindolyl group. / Inuki, Shinsuke; Oishi, Shinya; Fujii, Nobutaka; Ohno, Hiroaki.

In: Organic Letters, Vol. 10, No. 22, 2008, p. 5239-5242.

Research output: Contribution to journalArticle

Inuki, Shinsuke ; Oishi, Shinya ; Fujii, Nobutaka ; Ohno, Hiroaki. / Total synthesis of (±)-lysergic acid, lysergol, and isolysergol by palladium-catalyzed domino cyclization of amino allenes bearing a bromoindolyl group. In: Organic Letters. 2008 ; Vol. 10, No. 22. pp. 5239-5242.
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