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A synthetic approach to bicyclo[6.2.1]undecane ring systems

✍ Scribed by Mauricio Gomes Constantino; Kleber Thiago de Oliveira; Adilson Beatriz; Gil Valdo José da Silva

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
124 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

A synthesis of a functionalized bicyclo[6.2.1]undecane, N- (7-hydroxymethyl-bicyclo[6.2.1]undeca-3,5,9-trien-2-yl)-4methyl-benzenesulfonamide, is described. Starting with a [6+4] cycloaddition between cyclopentadiene and cycloheptatrienone, the final product was prepared in five steps with an overall 37% yield. The remarkable resistance to hydrolysis of an intermediate lactam was overcome by tosylating the amide and reducing with LiAlH 4 .

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