An intramolecular [2+2] photocycloaddition-fragmentation approach towards the total synthesis of asteriscanolide

Article abstract of DOI:10.1016/0040-4039(96)00224-9

A new route towards the Asteriscanolide skeleton is described. The key features include an efficient intramolecular [2+2] photocycloaddition of the α,β-unsaturated acid-ether 10 followed by a Curtius rearrangement/ ruthenium tetroxide/ fragmentation sequence to yield the cyclooctane lactones 13 and 14.