Biomimetic synthesis of carthamin, a red pigment in safflower petals, via oxidative decarboxylation,Journal of Heterocyclic Chemistry

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Biomimetic synthesis of carthamin, a red pigment in safflower petals, via oxidative decarboxylation
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2020-07-06 , DOI: 10.1002/jhet.4089
Yuka Abe ₁ , Takuo Sohtome ₁ , Shingo Sato ₁

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Carthamin, a natural red pigment derived from safflower, was discovered centuries ago and has been utilized in several industries such as dye, food coloring, and natural medicine industries. Although it has been used since Egyptian times, its structural features were only determined in the mid‐1900s when pioneering studies were conducted to elucidate the carthamin structure and assign its stereochemistry. Reproducing the complex biosynthesis of carthamin has been a common research goal since then. However, this has been rendered complex because of the unstable precursors and low yields from the multiple steps involved in the synthesis. Herein, we report the total synthesis of carthamin via a four‐step procedure using (S)‐C‐β‐D‐glucosylquinochalcone as the starting compound. The synthesis involves mild conditions, short reaction time, and readily available compounds. After de‐O‐methylation, condensation, oxidative decarboxylation, and saponification, carthamin was obtained in an overall yield of 9.5% through the proposed method.

中文翻译：

红花花瓣中的红色素红花素的氧化脱羧仿生合成

红花素是衍生自红花的天然红色颜料，几个世纪前就被发现，并已用于染料，食用色素和天然药物等多个行业。尽管它自埃及时代就已被使用，但其结构特征仅在1900年代中期才确定，当时进行了开创性研究以阐明红花素结构并确定其立体化学。从那时起，复制红花素的复杂生物合成一直是一个普遍的研究目标。然而，由于不稳定的前体和合成中涉及的多个步骤的低产率，这已经变得复杂。在此，我们通过（S）‐C ‐ β的四步法报告了红花素的总合成-D-葡萄糖基喹诺酮为起始化合物。该合成涉及温和的条件，较短的反应时间和易于获得的化合物。经过脱氧甲基化，缩合，氧化脱羧和皂化后，通过所提出的方法获得了红花素，总产率为9.5％。

更新日期：2020-07-06

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