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Issue 22, 1975
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Medium-ring 1,5-dienes. Part III. Cyclisation of germacra-1(10),4,7-(11)-triene oxides

Edward D. Brown,   James K. Sutherland  and  Teng W. Sam  

Abstract

The mono-oxides of germacra-1(10),4,7(11)-triene (1) have been prepared and an explanation is offered for the relative proportions obtained. Cyclisation of the 1,10-oxide yields selinane derivatives, whereas guaianes are obtained from the 4,5-oxide. Reductive cyclisation of the latter gives a guaiane, and on pyrolysis it is converted into a bicyclo[4.1.0]heptane derivative having the carbon skeleton found in the carabrone group of sesquiterpenes.

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Article information

https://doi.org/10.1039/P19750002332
J. Chem. Soc., Perkin Trans. 1, 1975, 2332-2336
Article type
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Medium-ring 1,5-dienes. Part III. Cyclisation of germacra-1(10),4,7-(11)-triene oxides

E. D. Brown, J. K. Sutherland and T. W. Sam, J. Chem. Soc., Perkin Trans. 1, 1975, 2332
DOI: 10.1039/P19750002332

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