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Assignment of Absolute Configuration of Bromoallenes by Vacuum-Ultraviolet Circular Dichroism (VUVCD)
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| Title: | Assignment of Absolute Configuration of Bromoallenes by Vacuum-Ultraviolet Circular Dichroism (VUVCD) |
| Authors: | Umezawa, Taiki Browse this author →KAKEN DB | | Mizutani, Nakaba Browse this author | | Matsuo, Koichi Browse this author →KAKEN DB | | Tokunaga, Yuugo Browse this author | | Matsuda, Fuyuhiko Browse this author →KAKEN DB | | Nehira, Tatsuo Browse this author →KAKEN DB |
| Keywords: | bromoallene | | structure determination | | VUVCD | | Lowe’s rule | | natural product |
| Issue Date: | 1-Mar-2021 |
| Publisher: | MDPI |
| Journal Title: | Molecules |
| Volume: | 26 |
| Issue: | 5 |
| Start Page: | 1296 |
| Publisher DOI: | 10.3390/molecules26051296 |
| Abstract: | A new application of vacuum-ultraviolet circular dichroism (VUVCD), which enables the measurement of CD spectra in the vacuum-ultraviolet region (140-200 nm), for the assignment of the absolute configurations of bromoallenes is described. Bromoallene moieties are found in natural products obtained from many marine organisms. To date, the absolute configuration of bromoallenes has been assigned almost exclusively with Lowe's rule, which is based on specific rotation. However, exceptions to Lowe's rule have been reported arising from the presence of other substituents with large specific rotations. For the unambiguous assignment of the absolute configuration of the bromoallene moiety with its characteristic absorption wavelength at 180-190 nm due to the pi-pi* transition, VUVCD was applied to four pairs of bromoallene diastereomers prepared by modifying the synthetic scheme of omaezallene. The VUVCD spectra clearly showed positive or negative Cotton effects around 180-190 nm according to the configuration of the bromoallene employed, revealing the potential of VUVCD for determining absolute stereochemistry. |
| Rights: | https://creativecommons.org/licenses/by/4.0/ |
| Type: | article |
| URI: | http://hdl.handle.net/2115/81343 |
| Appears in Collections: | 環境科学院・地球環境科学研究院 (Graduate School of Environmental Science / Faculty of Environmental Earth Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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