Abstract
| - Synthesis of the rearranged drimane sesquiterpenoids (+)-avaroland (+)-avarone from Wieland−Miescher ketone is described. This synthetic sequence providesconvenient access to the naturalenantiomers and, based on comparison of the optical rotation ofsynthetic avarol dimethyl etherwith literature data, affords material of significantly higher opticalrotation than a natural source.Similar synthetic strategies have been used to obtain severalrelated compounds, including a decalinbearing an exocyclic olefin and a highly substituted cyclohexane, thatcan be viewed as hybrids ofthe trans-fused avarol and cis-fused arenarol skeletons.
|