A CONCISE SYNTHESIS OF (E)-NEOMANOALIDES AND (Z)-NEOMANOALIDES

The first synthesis of(Z)-neomanoalide (4) and an improved synthesis o f its (E)-isomer 3 was accomplished in a concise, regiocontrolled mann er by exploiting yl)dimethylsiloxy]-4{[(tert-butyl)dimethylsiloxy]- me thyl}furan (6) as the key reagent. Lithiation of 6 and subsequent reac tion with the (2Z)- or (2E)-isomer of 2',6',6'-trimethylcyclohex-1'-en yl)nona-2,6-dienyl bromide (5), followed by hydrolysis, afforded the c orresponding neomanoalide.