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Nitro-Mannich reaction and intramolecular 1,3-dipolar cycloaddition route to acylpyrrolidinones: Synthesis of a tetramic acid and (+)-laccarin |
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| Authors: | Ryo Katsuta Hiroki Ichijo Ginka Oouchi Arata Yajima Ken Ishigami Tomoo Nukada |
| Institution: | 1. Department of Chemistry for Life Sciences and Agriculture, Tokyo University of Agriculture, 1-1-1 Sakuragaoka, Setagaya-ku, Tokyo 156-8502, Japan;2. Graduate School of Agriculture, Tokyo University of Agriculture, 1-1-1 Sakuragaoka, Setagaya-ku, Tokyo 156-8502, Japan;3. Department of Fermentation Science, Tokyo University of Agriculture, 1-1-1 Sakuragaoka, Setagaya-ku, Tokyo 156-8502, Japan |
| 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. |
| Keywords: | 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 |
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