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Intramolecular [4+2] cycloaddition reactions of enamines and enamides

✍ Scribed by Stephen F. Martin; Ta-shue Chou; Chih-yun Tu

Publisher
Elsevier Science
Year
1979
Tongue
French
Weight
259 KB
Volume
20
Category
Article
ISSN
0040-4039

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✦ Synopsis

An attempt to utilize a new strategy for alkaloid synthesis which features the intramolecular [4+2] cycloaddition of enamines and enamides for the construction of the tetracyclic spiroamine skeleton characteristic of the ~rythrina alkaloids was unsuccessful, unexpectedly giving a bridged cycloadduct rather than a fused one. The hydroindole and hydroquinoline ring systems are common to a diverse array of alkaloid natural products.

πŸ“œ SIMILAR VOLUMES

Intramolecular [4+2]-cycloaddition react
Intramolecular [4+2]-cycloaddition reactions of cyclic 2-thiomethyl-5-amidofurans
✍ John D Ginn; Stephen M Lynch; Albert Padwa πŸ“‚ Article πŸ“… 2000 πŸ› Elsevier Science 🌐 French βš– 85 KB

Cyclic 2-thiomethyl-5-amidofurans possessing tethered p-bonds were prepared by a dimethyl(methylthio) sulfonium tetrafluoroborate (DMTSF) induced cyclization of various amido dithioacetals. Upon heating, these systems undergo an intramolecular 4+2-cycloaddition reaction. The initially formed Diels-A