posted on 1996-12-13, 00:00authored byJianguo An, David F. Wiemer
Synthesis of the rearranged drimane sesquiterpenoids (+)-avarol
and (+)-avarone from Wieland−Miescher ketone is described. This synthetic sequence provides
convenient access to the natural
enantiomers and, based on comparison of the optical rotation of
synthetic avarol dimethyl ether
with literature data, affords material of significantly higher optical
rotation than a natural source.
Similar synthetic strategies have been used to obtain several
related compounds, including a decalin
bearing an exocyclic olefin and a highly substituted cyclohexane, that
can be viewed as hybrids of
the trans-fused avarol and cis-fused arenarol skeletons.