The synthesis of alkaloids using transition-metal-catalyzed intramolecular amination reactions

Hiroaki Ohno, Hiroaki Chiba, Shinsuke Inuki, Shinya Oishi, Nobutaka Fujii

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Transition-metal-catalyzed reactions have the potential to provide significant improvements to the syntheses of complex target molecules. These reactions can be used to achieve a variety of different atom-economical transformations and cascade reactions and, therefore, provide access to synthetic strategies that would otherwise be unavailable using classical organic chemistry. To exemplify the utility of the latest transition-metal-catalyzed reactions for the construction of important target structures, we have been involved in the total synthesis of natural products bearing widely known chemical scaffolds. In this account, we report our recent studies on the use of a palladium-catalyzed cascade cyclization reaction and a gold(I)-catalyzed hydroamination reaction for the construction of the core structures of alkaloids, as well as their application to the total syntheses of lysergic acid, lysergol, isolysergol, and quinocarcin. 1 Introduction 2 Ergot Alkaloid Synthesis 2.1 Construction of the Core Structure by Palladium-Catalyzed Cascade Cyclization 2.2 Asymmetric Total Syntheses of (+)-Lysergic Acid and ÂRelated Alkaloids 3 Quinocarcin Synthesis 3.1 Construction of the Core Structure by Gold-Catalyzed ÂHydroamination 3.2 Asymmetric Total Synthesis of (-)-Quinocarcin 4 Concluding Remarks

Original languageEnglish
Article numberST-2013-A0781-A
Pages (from-to)179-192
Number of pages14
JournalSynlett
Volume25
Issue number2
DOIs
Publication statusPublished - 2014 Jan
Externally publishedYes

Fingerprint

Amination
Alkaloids
Transition metals
Lysergic Acid
Cyclization
Palladium
Gold
Bearings (structural)
Ergot Alkaloids
Biological Products
Scaffolds
Atoms
Molecules

Keywords

  • alkaloids
  • atom economy
  • gold
  • palladium
  • total synthesis

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Ohno, H., Chiba, H., Inuki, S., Oishi, S., & Fujii, N. (2014). The synthesis of alkaloids using transition-metal-catalyzed intramolecular amination reactions. Synlett, 25(2), 179-192. [ST-2013-A0781-A]. https://doi.org/10.1055/s-0033-1340165

The synthesis of alkaloids using transition-metal-catalyzed intramolecular amination reactions. / Ohno, Hiroaki; Chiba, Hiroaki; Inuki, Shinsuke; Oishi, Shinya; Fujii, Nobutaka.

In: Synlett, Vol. 25, No. 2, ST-2013-A0781-A, 01.2014, p. 179-192.

Research output: Contribution to journalArticle

Ohno, H, Chiba, H, Inuki, S, Oishi, S & Fujii, N 2014, 'The synthesis of alkaloids using transition-metal-catalyzed intramolecular amination reactions', Synlett, vol. 25, no. 2, ST-2013-A0781-A, pp. 179-192. https://doi.org/10.1055/s-0033-1340165
Ohno, Hiroaki ; Chiba, Hiroaki ; Inuki, Shinsuke ; Oishi, Shinya ; Fujii, Nobutaka. / The synthesis of alkaloids using transition-metal-catalyzed intramolecular amination reactions. In: Synlett. 2014 ; Vol. 25, No. 2. pp. 179-192.
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