Formal total synthesis of (+)-lysergic acid via zinc(II)-mediated regioselective ring-opening reduction of 2-alkynyl-3-indolyloxirane

Akira Iwata, Shinsuke Inuki, Shinya Oishi, Nobutaka Fujii, Hiroaki Ohno

Research output: Contribution to journalArticle

38 Citations (Scopus)

Abstract

Asymmetric formal synthesis of (+)-lysergic acid was achieved with a reductive ring-opening reaction of chiral 2-alkynyl-3-indolyloxirane with NaBH3CN as the key step. With Zn(OTf)2 as an additive, the ring-opening reaction proceeded regioselectively at the 3-position to give the corresponding propargyl alcohol, which was a precursor of the allenic amide for palladium-catalyzed domino cyclization to construct the ergot alkaloid core structure.

Original languageEnglish
Pages (from-to)5506-5512
Number of pages7
JournalJournal of Organic Chemistry
Volume76
Issue number13
DOIs
Publication statusPublished - 2011 Jul 1
Externally publishedYes

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Lysergic Acid
Ergot Alkaloids
Cyclization
Palladium
Amides
Zinc
propargyl alcohol

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Formal total synthesis of (+)-lysergic acid via zinc(II)-mediated regioselective ring-opening reduction of 2-alkynyl-3-indolyloxirane. / Iwata, Akira; Inuki, Shinsuke; Oishi, Shinya; Fujii, Nobutaka; Ohno, Hiroaki.

In: Journal of Organic Chemistry, Vol. 76, No. 13, 01.07.2011, p. 5506-5512.

Research output: Contribution to journalArticle

Iwata, Akira ; Inuki, Shinsuke ; Oishi, Shinya ; Fujii, Nobutaka ; Ohno, Hiroaki. / Formal total synthesis of (+)-lysergic acid via zinc(II)-mediated regioselective ring-opening reduction of 2-alkynyl-3-indolyloxirane. In: Journal of Organic Chemistry. 2011 ; Vol. 76, No. 13. pp. 5506-5512.
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