95(P33) ベニバナの水溶性黄色色素成分の絶対構造(ポスター発表の部)

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Planar structures of the five yellow coloring matters of safflower (Carthamus tinctorius L.) have recently been elucidated. In our continuing search for these compounds, the absolute structures of these five coloring matters(2〜6) were investigated. The compounds 2〜6 have a common asymmetric carbon at C* position in their molecule and the compounds 4 and 5 have another asymmetric carbon at C** position (scheme 1). Each of these coloring matters gave no single crystals for X-ray crystallographic analysis. A cid hydrolysis and subsequent methylation of 4 and 5 yielded the chalcone type derivatives 8a(+66°) and 8b(-66°) as a viscous oil, respectively. On the other hand, two enantiomers, 8R(+61°) and 8S(-75°), were synthesized by the method described in scheme 2. The spectral data of 8a and 8b were completely identical with those of synthetic 8R and 8S, respectively. This result confirmed that the absolute configuration of C** were R in 4 and Sin 5. The X-ray crystallographic analysis of heptaacetate of 4 showed that the absolute configuration of 4 at C* position is S, but the heptaacetate of 5 gave no single crystal. So, two model compounds 17a(C*=S) and 17b(C*=R) were synthesized by the method described in scheme 3. The absolute configuration of C* of 5 was elucidated as S by the comparison of its CD spectrum with those of 4 and synthetic 17a and 17b. The absolute configurations of C* of the other yellow coloring matters 2, 3 and 6 were also elucidated as S by the investigation of their CD spectra.
天然有機化合物討論会の論文
1997-07-20

95(P33) ベニバナの水溶性黄色色素成分の絶対構造(ポスター発表の部)

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