Journal of the Chemical Society C: Organic

The garryfoline–cuauchichicine rearrangement: a study of the mechanism in the (–)-kaurenols

MF Barnes, J MacMillan

Index: Barnes,M.F.; MacMillan,J. Journal of the Chemical Society [Section] C: Organic, 1967 , p. 361 - 366

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Citation Number: 13

Abstract

The mechanism of the garryfoline–cuauchichicine rearrangement has been investigated using the epimeric (–)-kaur-16-en-15-ols as models. The 15β-ol is shown to rearrange rapidly in mineral acid at room temperature to 16R-(–)-kaur-15-one by a 15, 16-hydride shift. The 16α-ol, like veatchine, is stable under these conditions. The contrast in the ability of these epimeric alcohols to undergo 15, 16-hydride shifts is discussed. Under the same ...