The Journal of Organic Chemistry

Synthesis of (+-)-geosmin and the other 1, 10-dimethyl-9-decalol isomers

JA Marshall, AR Hochstetler

Index: Marshall,J.A.; Hochstetler,A.R. Journal of Organic Chemistry, 1968 , vol. 33, p. 2593 - 2595

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Citation Number: 49

Abstract

modification of Gerber and Lechevalier's geosmin. We previously found that the methyl octalin 1 affords a 57: 43 mixture of the trans and cis-decalin oxipanes 2 and 3 upon treatment with m-chloroperoxybenzoic acid in benzene (Scheme I). 5 This mixture slowly reacted with methylmagnesium bromide in refluxing tetrahydrofuran to give decalols 5 and 6 which could be separated by careful chromatography on Flori-siL5 The dimethyloctalin 7 ...

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