Abstract
A new total synthesis of the chamigrene sesquiterpenoids (Z )-9-(bromomethylene)-1,5,5-trimethylspiro[5.5]undeca-1,7-diene-3-one
and its 15-E -epimer has been accomplished
in 13 steps. In our sequence, a Diels-Alder reaction and
subsequent reductive alkylation of the resulting adduct was utilized
as the key strategy to create the A-ring and the quaternary spirocenter
with the suitable functionalities for accessing the B-ring. Additionally,
from the advanced intermediate, a total synthesis of (±)-majusculone,
a nor-chamigrene natural product, was also readily achieved in two steps.
Key words
chamigrenes - sesquiterpenes - majusculone - total syntheses - Diels-Alder reaction
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