Nitro-Mannich reaction and intramolecular 1, 3-dipolar cycloaddition route to acylpyrrolidinones: Synthesis of a tetramic acid and (+)-laccarin. Issue 24 (13th June 2018)

• Record Type: Journal Article
• Authors: Katsuta, Ryo; Ichijo, Hiroki; Oouchi, Ginka; Yajima, Arata; Ishigami, Ken; Nukada, Tomoo
• Is Part Of: Tetrahedron letters. Volume 59:Issue 24(2018)
• Page Start: 2352
• Page End: 2355
• Publication Date: 2018-06-13
• Subjects: DAMBAJDWLIFTNW-YLWLKBPMSA-N -- IYCRUIBTQMWYEC-VURMDHGXSA-N -- MMIRZQYFOOFFNP-UHFFFAOYSA-N -- KCRHGOPVLCDATD-UHFFFAOYSA-N -- IMONJFPOPMHUMZ-UHFFFAOYSA-N -- SOJBQUPYBWUOSQ-UHFFFAOYSA-N; Pyrrolidinone -- Tetramic acid -- Laccarin -- Nitro-Mannich reaction -- Cycloaddition; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.05.014
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Alternative synthetic pathway to acylpyrrolidinones. Nitro-Mannich/1, 3-diplar cycloaddition reactions of simple carbon sources. Concise synthesis of the natural tetramide (+)-laccarin. Abstract: An efficient synthetic pathway to acylpyrrolidinones via a nitro-Mannich reaction, followed by the intramolecular 1, 3-dipolar cycloaddition of a nitrile oxide to an alkyne was developed. The syntheses of a leucine-derived tetramic acid and natural tetramide (+)-laccarin were achieved in five steps using aldehydes, 2-alkynamides and nitromethane as the carbon sources.