Abstract
The natural coumarins, sesibiricin ( 1) and toddaculin ( 28) have been synthesised from 5,7-dihydroxycoumarin, the former by a sequence involving regioselective O-prenylation at C-5 and C-prenylation at C-8. The prenyl ether of 5-hydroxy-7-methoxycoumarin, a key intermediate in the synthesis of toddaculin, has been found to undergo Claisen rearrangement exclusively to the para position thereby providing an alternative route to sesibiricin.
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