91 ワサビジエノン-Aの合成研究(ポスター発表の部)

概要

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Five yellow pigments, new natural cyclohexadienone derivatives, isolated from potato culture solution of Phoma wasabiae YOKOGI by Soga et al. One of them, Wasabidienone-A (WA) was firstly determined to be a tautomeric mixture (1a, 1b) by ^1H NMR analysis of each methyl ethers and acetates. After that, these structures were revised as a mixture of 2a and 2b by X-ray analysis of benzoate (2b') of one of the tautomers. This characteristic tautomerism of WA prompted us to study from the site of synthesis. At first, we synthesized each methyl ethers of WA, via novel intramolecular 1, 3-acylrearrangement. We also examined about this novel rearrangement in detail. Spectra of two of the three methyl ethers were identified with those of natural WA, respectively. Here, we established that WA is a tautomeric mixture of 2a and 2b by the synthesis of each methyl ether of the tautomer. Further, our attempt for synthesis of WA is now in progress by regioselective protecting of the enol-hydroxyl group of 11.
天然有機化合物討論会の論文
1992-09-10