Total synthesis of the proposed structure for aromin and its structural revision.
Total synthesis of the proposed structure for aromin and its structural revision.
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所提出的芳香素结构的全合成及其结构修正。
DOI：
10.1021/acs.joc.6b02187
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发表时间：
2016
期刊：
影响因子：
--
通讯作者：
Koshino H.
中科院分区：
文献类型：
--
作者：
Takahashi S;Satoh D;Hayashi M;Takahashi K;Yamaguchi K;Nakamura T;Koshino H.
本文首次合成了芳香素及其4S， 7r -异构体。芳香素是一种具有罕见的双thf环体系的无机乙酰原素。关键步骤包括一对末端二烯醇的氧化环化和烯酮携带四氢呋喃内酯的烯基四氢呋喃的分子间复分解。两种样品的光谱数据都不匹配。利用CAST/CNMR结构解析器和化学衍生物重新检查核磁共振数据表明，芳烃的真实结构应该被修改为四氢吡喃乙酰素，蒙他那酸D.合成样品在人实体瘤细胞系中的细胞毒性也进行了评估。
This paper describes the first total synthesis of the proposed structure for aromin, an annonaceous acetogenin possessing an unusual bis-THF ring system, and its 4S,7R-isomer. The key steps involve an oxidative cyclization of a couple of terminal-diene alcohols and an intermolecular metathesis of an alkenyl tetrahydrofuran with an enone carrying a tetrahydrofuranyl lactone. The spectral data of both samples did not match those of aromin. Re-examination of the NMR data using the CAST/CNMR Structure Elucidator and chemical derivations suggested that the real structure of aromin should be revised to be a tetrahydropyran acetogenin, montanacin D. Cytotoxicities in human solid tumor cell lines for synthetic samples were also evaluated.