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Synthesis and Characterization of Diastereoisomerically Pure Tetracyclo[6.2.1.13,6.02,7]dodec-9-ene-4-carboxylic Acid Derivatives

✍ Scribed by Timo Rager; C. Grant Willson


Publisher
John Wiley and Sons
Year
2000
Tongue
German
Weight
195 KB
Volume
83
Category
Article
ISSN
0018-019X

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✦ Synopsis


The synthesis and detailed NMR analysis of diastereoisomerically pure samples of 4-methyltetracyclo[6.2.1.1 3,6 .0 2,7 ]dodec-9-ene-4-carboxylic acid (2), tetracyclo[6.2.1.1 3,6 .0 2,7 ]dodec-9-ene-4-carboxylic acid ( ) and their tert-butyl esters are reported. Mixtures containing two isomers of the methyl esters of these compounds were obtained by a twofold, sequential Diels-Alder reaction between cyclopentadiene, and methyl methacrylate or methyl acrylate, respectively. Pure diastereoisomers of the acids were prepared by selective hydrolysis of their methyl esters.


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