Synthesis of functionalized trienes and regioselective formation of medium-ring lactones through intramolecular Diels-Alder reaction

Journal of Organic Chemistry

Volumn 61, Issue 21, 1996, Pages 7597-7599

  Deagostino, Annamaria ^a   Maddaluno, Jacques ^b   Prandi, Cristina ^a   Venturello, Paolo ^a  

^a UNIVERSITY OF TURIN   (Italy)

^b UNIVERSITÉ DE ROUEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000661101     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960876h     Document Type: Article

References (34)

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16. (E)-1-Ethoxybuta-1,3-diene and N-methylmaleimide at reflux in toluene under argon, in the presence of hydroquinone, afforded after 1 h N-methyl-3-ethoxycyclohex-4-ene-1,2-dicarboxamide (50%).
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28. The gem-dialkyl effect in seven to eleven-membered ring clousure by iodolactonization has also been observed: Simonot, B.; Rousseau, G. Tetrahedron Lett. 1993, 34, 4527.
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31. We have checked that the primary 67:33 mixture obtained from decalin isomerizes quickly when placed into refluxing benzonitrile.
32. We thank one of the referees for this suggestion. A retro-Diels-Alder sequence can also be evoked. See in relation: Zylber, J.; Tubul, A.; Brun, P. Tetrahedron Asymm. 1995, 6, 377.
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