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

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40 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

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ASJC Scopus subject areas

  • Organic Chemistry

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