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Stereoselective intramolecular Diels–Alder reactions of 3-alkenyl(oxy)-2(1H)-pyrazinones

✍ Scribed by Wim M. De Borggraeve; Frederik J.R. Rombouts; Bie M.P. Verbist; Erik V. Van der Eycken; Georges J. Hoornaert

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 78 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)02188-8

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✦ Synopsis

Dichloropyrazinones are reacted with alkenolates or a Grignard reagent in order to tether a dienophilic side-chain at the 3-position. The compounds smoothly undergo intramolecular Diels-Alder reaction forming tricyclic ring systems. The reactions proceed completely stereoselective yielding only endo adducts. In the case of the alkenylpyrazinone, the core skeleton of the breviamides is obtained.

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## Abstract For Abstract see ChemInform Abstract in Full Text.