Synthesis of a neoatisiranone, the enantiomer of a ketone obtained by the acid-catalysed rearrangement of isophyllocladene epoxide
Abstract
The constitution and stereochemistry of a compound obtained by the acid-catalysed rearrangement of isophyllocladene epoxide have been confirmed by a synthesis of its enantiomer from (–)-neoatisirene. In addition, it has been shown that the neoatisiranol (XII) on dehydration undergoes skeletal rearrangement to the olefin (XIII).