84 光学活性ウドテアトリアールの合成とその絶対配置の決定(ポスター発表の部)
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Udoteatrial (1) isolated from marine algae Udotea flabellum is an unique diterpenoid having three aldehyde groups in it. Since all three substituents on the 5-membered ring are in cis configuration, 1 is known to exist as a form of mono-hydrate, udoteatrial hydrate (2). The relative stereochemistry of 2 was settled down by a total synthesis of racemic 2 by Whitesell et al., but the absolute configuration was still remained uncertain. We have been investigating the synthesis of biologically active iridoids as well as maring natural products starting from (+)-genipin (4), which could be obtained in an industrial scale. Since the tricyclic portion of 2 could be assumed as a mono-terpene iridoid skeleton, we were interested in the synthesis of 2 from 4 to determine the absolute configuration and furthermore to look at the effect of side chain in the structure-activity relationship. The exomethylene lactone (5) was designated to be a common intermediate for the synthesis of 2 as well as various analogues having different side chains. The stereochemistry at C-7 position after introduction of side chain into 5 was carefully studied by comparing their ^1H-NMR spectra with those of model compounds, of which stereochemistry was confirmed by single crystal X-ray determination. Having finished the synthesis of diacetate of 2, comparison of the sign of optical rotation between synthetic and natural diacetate revealed that the natural udoteatrial was the enantiomer of that we synthesized. Thus we concluded that the absolute structure of natural 2 was depicted as (24) having 2R, 3S, 6S and 7S configuration.
- 天然有機化合物討論会の論文
- 1992-09-10
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