Enantiopure building blocks for marine natural products via differentiation of enantiotopic groups

Article abstract of DOI:10.1016/S0040-4020(98)00158-6

The group and face-selective cycloaddition of the enantiopure cyclopentadiene 4 to the tyrosine-related spirocylohexadienone 10 provided a high yield of the enantiomencally pure cyclohexadienone 11. Stereoselective transformations at the remaining double bond followed by a thermal retro- process, finally giving rise to the chromophore of the marine agelorin antibiotics isolated from the sponge Agelas oroides Schmidt.