Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
A Synthesis of (±)-β-Vetivone and Its Related Spirovetivanes via the Base-catalyzed Spiroannelation of Phenolic Tosylates
Sigeru ToriiKenji UneyamaKaoru Okamoto
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1978 Volume 51 Issue 12 Pages 3590-3594

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Abstract

(±)-β-Vetivone was synthesized by the base-catalyzed spiroannelation of 2-[2-(4-hydroxy-2-methylphenyl)-ethyl]-3-methyl-3-butenyl p-toluenesulfonate followed by methylation and subsequent isomerization of the side chain double bond. The reactivities of the related tosylates, 4-(4-hydroxy-2-methylphenyl)-2-isopropylbutyl p-toluenesulfonate, 3-hydroxy-2-[2-(4-hydroxy-2-methylphenylethyl]-3-methylbutyl p-toluenesulfonate, and 2,3-epoxy-2-[2-(4-hydroxy-2-methylphenyl)ethyl]-3-methylbutyl p-toluenesulfonate have been discussed.

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