Synthesis and structural revision of a brominated sesquiterpenoid, aldingenin C
Shunya Takahashi1, Masayuki Yasuda, Takemichi Nakamura
1RIKEN , Wako, Saitama 351-0198, Japan.
Abstract:
This paper describes a short step synthesis of the proposed structure for aldingenin C from trans-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.
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