| Title: |
Synthesis and Structural Revision of a Brominated Sesquiterpenoid, Aldingenin C. |
| Authors: |
Shunya Takahashi1 shunyat@riken.jp, Masayuki Yasuda1,2, Takemichi Nakamura1, Ken Hatano2, Koji Matsuoka2, Hiroyuki Koshino1 koshino@riken.jp |
| Source: |
Journal of Organic Chemistry. 10/3/2014, Vol. 79 Issue 19, p9373-9380. 8p. |
| Subject Terms: |
*LIMONENE, *TETRAHYDROPYRANYL compounds synthesis, *INTRAMOLECULAR charge transfer, *EPOXY compounds, *RING formation (Chemistry) |
| 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. [ABSTRACT FROM AUTHOR] |
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| Database: |
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