Synthesis and Structural Revision of a Brominated Sesquiterpenoid, Aldingenin C

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• 作者：Shunya Takahashi ; Masayuki Yasuda ; Takemichi Nakamura ; Ken Hatano ; Koji Matsuoka ; Hiroyuki Koshino
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：October 3, 2014
• 年：2014
• 卷：79
• 期：19
• 页码：9373-9380
• 全文大小：374K
• ISSN：1520-6904

文摘

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.