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Synthesis of decalin synthons of bioactive terpenoids: Lewis acid catalyzed Diels-Alder reactions

โœ Scribed by T. Mayelvaganan; Shreeshailkumar B. Hadimani; Sujata V. Bhat


Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
189 KB
Volume
53
Category
Article
ISSN
0040-4020

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โœฆ Synopsis


Diels-Alder reaction of 1,3,3-trimethyl-2-vinylcyclohexene I with conjugated ketones 2 -7 in the presence of Lewis acid leads to regto-and stereo-selective formation of bicyclic adducts 8 -13 versatile intermediates to labdanes, abietane and spongian diterpenoids.


๐Ÿ“œ SIMILAR VOLUMES


On the mechanism of Dielsโ€”Alder reaction
โœ V. Branchadell; A. Oliva; J. Bertran ๐Ÿ“‚ Article ๐Ÿ“… 1985 ๐Ÿ› Elsevier Science ๐ŸŒ English โš– 261 KB

The effect of Lewis acid catalysts on the mechanism of Diels-Alder reactions is studied using the MINDO/3 method. It is found that they tend to increase the two-step character of the process through a more important participation of the charge-transfer configuration.

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6-Vinylpurines readily undergo Diels-Alder reactions with dienes. Both reactivity and endo selectivity are greatly improved when the cycloadditions are performed in the presence of zinc chloride. Lewis acid mediated Diels-Alder reaction of 6-vinylpurine riboside was employed as a key step in the syn