胡桃霉素及其衍生物合成的统一方法。
Unified Approach toward Syntheses of Juglomycins and Their Derivatives.
作者信息
Yoshioka Kai, Kamo Shogo, Hosaka Keisuke, Sato Ryohei, Miikeda Yuma, Manabe Yuri, Tomoshige Shusuke, Tsubaki Kazunori, Kuramochi Kouji
机构信息
Graduate School for Life and Environmental Sciences, Kyoto Prefectural University, 1-5 Shimogamo Hangi-cho, Sakyo-ku, Kyoto 606-8522, Japan.
Department of Applied Biological Science, Faculty of Science and Technology, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan.
出版信息
ACS Omega. 2019 Jul 5;4(7):11737-11748. doi: 10.1021/acsomega.9b01376. eCollection 2019 Jul 31.
A unified and common intermediate strategy for syntheses of juglomycins and their derivatives is reported. The use of a 1,4-dimethoxynaphthalene derivative as a key intermediate enabled easy access to various juglomycin derivatives. In this study, juglomycins A-D, juglomycin C amide, khatmiamycin and its 4-epimer, and the structure proposed for juglomycin Z were synthesized from this intermediate. The absolute configuration of natural khatmiamycin has been established to be 3,4 through our synthesis. Unfortunately, the spectroscopic data for synthetic juglomycin Z were not consistent with the data reported for the natural one, strongly suggesting a structural misassignment.
报道了一种用于合成胡桃霉素及其衍生物的统一且通用的中间策略。使用1,4 - 二甲氧基萘衍生物作为关键中间体能够轻松获得各种胡桃霉素衍生物。在本研究中，从该中间体合成了胡桃霉素A - D、胡桃霉素C酰胺、卡塔霉素及其4 - 差向异构体，以及为胡桃霉素Z提出的结构。通过我们的合成确定了天然卡塔霉素的绝对构型为3,4。不幸的是，合成的胡桃霉素Z的光谱数据与报道的天然产物数据不一致，这强烈表明结构归属有误。
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