Nonenzymic biogenetic-like cyclizations. Synthesis and cyclization of 4-(trans, trans-7, 12-dimethyl-3, 7-11-tridecatrienyl)-3-methyl-2-cyclohexen-1-ol and of its allylic …

KA Parker, WS Johnson

Index: Parker,K.A.; Johnson,W.S. Journal of the American Chemical Society, 1974 , vol. 96, p. 2556 - 2563

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Citation Number: 19

Abstract

Abstract: The aim of this study was to synthesize the tetraenols 5 and 6 in the hope that they could be induced to undergo acid-catalyzed cyclization to produce products derived from the tetracyclic carbonium ion 7. Substrate 5 was synthesized by the sequence outlined in Scheme 11, the key step being the coupling of the lithium acetylide of 14 with the bromodiene 13 (prepared according to Scheme I). Substrate 6 was produced by the ...