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Synthetic study of a moss-produced oxylipin and its structural revision

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Citation

Soedaa, H., Towadaa, R., Oguraa, Y., Mohria, T., Pohnert, G., & Kuwaharaa, S. (2019). Synthetic study of a moss-produced oxylipin and its structural revision. Tetrahedron, 75(11), 1555-1562. doi:10.1016/j.tet.2019.02.012.


Cite as: https://hdl.handle.net/21.11116/0000-0003-AE05-4
Abstract
The proposed structure for a moss-produced acetylenic oxylipin (10-keto-type structure) was synthesized from a known glycidol derivative by an 11-step sequence involving epoxide ring opening with a terminal acetylene and enzymatic hydrolysis of a methyl ester intermediate. The NMR spectra of the proposed structure was, however, different from those of the natural oxylipin, which prompted us to synthesize its 9-epi-isomer and two diastereomeric 12-keto-type positional isomers. Comparison of the NMR spectra of the three isomers with those of the natural oxylipin indicated that the natural oxylipin was actually a mixture of the two diastereomeric positional isomers.