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The Lewis acid-promoted rearrangement of two 10-methyl-4,5-epoxydecalins bearing a trimethylsilyl (TMS) group on C-1 or C-9 has been studied. Migration of the C-9 methylene group to C-5 is the major reaction pathway when the TMS and the oxirane groups are on the same ring while methyl migration results exclusively when they are on different rings.
This article reports on the transformation of santonin into two C 10 -epimeric 3-oxa-guaianolides which are 8-deoxyderivatives of several natural 3-oxaguaianolides isolated from Achillea species. The synthesis involved the photochemical rearrangement of the eudesmane skeleton into a guaiane skeleton and the transformation of the cyclopentane ring into a furan moiety with the concomitant...
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