The rearrangement of some epoxy podocarpanoic acids
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Rearrangement of the epoxides derived from the podocarpenoic acids (3b), (3d) and (5b) with boron trifluoride etherate gave compounds with the rosane skeleton, lacking substituents at C 13. The rearrangement involves the shift of a methyl group with concomitant lactonization. The unsaturated acids (3b) and (5b) undergo similar rearrangements when they are treated with boron trifluoride etherate or sulphuric acid.
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Australian Journal of Chemistry