Total synthesis of the alkoxydioxines (+)- and (-)-chondrillin and (+)- and (-)-plakorin via singlet oxygenation/radical rearrangement

The photoisomerization of the 4-peroxy-2-enones via singlet oxygenation and peroxy radical rearrangement was applied to the total synthesis of the alkoxydioxine natural products chondrillin and plakorin. Analysis of the optical rotation of the synthetic material indicated that both chondrillin and plakorin are either enantiomerically pure or highly enriched in one enantiomer. Results also showed that the configuration of chondrillin in past literature is erroneous.