Tetrahedron

Use of the ketel claisen rearrangement for the synthesis of cyclic sesquiterpenes containing quaternary centers. A formal synthesis of cuparene

PF Schuda, SJ Potlock, H Ziffer

Index: Schuda, Paul Francis; Potlock, Steven J.; Ziffer, Herman Tetrahedron, 1987 , vol. 43, # 3 p. 463 - 468

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Citation Number: 20

Abstract

We have shown that the ketal based Claisen rearrangement can be useful for generating vicinal quaternary and tertiary-quaternary centers by suitable substitution on the reacting 2- cyclohexenols and cycloalkanone ketal. A rapid and efficient method for preparing hindered cycloalkanone ketals in very pure form is presented, as well as a useful modification for synthesizing the required 2-cyclohexenols from alkyl anisoles with a minimum number of ...