Synthesis and Structural Revision
of a Brominated
Sesquiterpenoid, Aldingenin C
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Abstract
This
paper describes a short step synthesis of the proposed structure
for aldingenin C from <i>trans</i>-limonene oxide. The tetrahydropyran-fused
2-oxabicyclo[3.2.2]nonane skeleton as the structural feature was constructed
by an intramolecular epoxide-opening reaction and a brominative cyclization.
The spectral data of the synthetic compound did not match those of
the natural product reported. Re-examination of the reported NMR data
using new CAST/CNMR Structure Elucidator suggests that the structure
of aldingenin C should be revised to that of known caespitol
