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Synthesis of chiral trans-syn-cis and trans-anti-trans [6.6.6] tricycles by transannular Diels-Alder reaction

✍ Scribed by Rico Lavoie; András Toró; Pierre Deslongchamps

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 892 KB
Volume: 55
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(99)00796-6

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✦ Synopsis

Stereocontrolled asymmetric synthesis and transannular Diels-Alder (TADA) reaction of a 14-membered transcis-cis (TCC) macrocyclic trienone with an activated dienophile leading to an A.B.C [6.6.6] tricycle having one angular methyl group is reported. The results of thermal and Lewis acid catalyzed TADA reaction are discussed.

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