A Concise Synthesis of ( E )‐ and ( Z )‐Neomanoalides

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 (2 Z )‐ or (2 E )‐isomer of (6 E )‐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.