HOWELL RESEARCH GROUP

DEPARTMENT OF CHEMISTRY
UNIVERSITY OF CONNECTICUT

 

Total Synthesis of Laureatin

Another project exploiting the reactivity of 1,5-dioxoaspiro[3.2]hexanes is our effort to synthesize laureatin, a metabolite isolated from the Laurencia red algae L. nipponica. This metabolite has shown strong activity as a mosquito larvicide. Our retrosynthetic approach is shown in Scheme 1.

 

At present, the eneyne adduct 14 has been prepared utilizing the Sonogashira coupling of a haloalkene with an alkyne. We also have prepared compound 15 from the ring opening of 1,5-dioxoaspiro[3.2]hexanes 16 with DIBAL-H.