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

Author:
Soeda, Hiroki, Towada, Ryo, Ogura, Yusuke, Mohri, Tomoyo, Pohnert, Georg, Kuwahara, Shigefumi
Source:
Tetrahedron 2019 v.75 no.11 pp. 1555-1562
ISSN:
0040-4020
Subject:
acetylene, chemical reactions, enzymatic hydrolysis, glycidol, nuclear magnetic resonance spectroscopy, oxylipins, positional isomers
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.
Agid:
6306784