231. “A Concise Synthesis of (E)- and (Z)-Neomanoalides”
     Jefford, C.W.; Rossier, J.-C.; Boukouvalas, J.; Huang, P.
     Helv. Chim. Acta 1994, 77, 661-667.

The first synthesis of (Z)-neomanoalide (4) and an improved synthesis of its (E)-isomer 3 was accomplished in a concise, regiocontrolled manner by exploiting 2-[(tert-butyl)dimethylsiloxy]-4{[(tert-butyl)dimethylsiloxy]-methyl}furan (6) as the key reagent. Lithiation of 6 and subsequent reaction with the (2Z)- or (2E)-isomer of (6E)-3-{[(tert-butyl)dimethylsiloxy]methyl}-7-methyl-9-(2′,6′,6′-trimethylcyclohex-1′-enyl)nona-2,6-dienyl bromide (5), followed by hydrolysis, afforded the corresponding neomanoalide.

DOI : 10.1002/hlca.19940770309 

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