(-)-香豆异呋巴因、(-)-香豆异呋巴醇、(-)-12--香豆异呋巴醇以及 (-)-毛蕊异呋巴因 A 和 B 的全合成：使用金（I）催化的环化策略。
Total Synthesis of (-)-Citreoisocoumarin, (-)-Citreoisocoumarinol, (-)-12--Citreoisocoumarinol, and (-)-Mucorisocoumarins A and B Using a Gold(I)-Catalyzed Cyclization Strategy.
机构信息
Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
Academy of Scientific and Innovative Research (AcSIR), New Delhi 110025, India.
出版信息
J Org Chem. 2020 Mar 20;85(6):4122-4129. doi: 10.1021/acs.joc.9b03278. Epub 2020 Mar 10.
A unified and concise first asymmetric total synthesis of (-)-citreoisocoumarin (), (-)-citreoisocoumarinol (), 12--citreoisocoumarinol (), and (-)-mucorisocoumarins A () and B () have been accomplished from the common intermediate (-)-6--methyl-citreoisocoumarin (). Central to the synthetic approach is a regioselective gold(I)-catalyzed 6-- cyclization strategy for the construction of the isocoumarin skeleton. The other key steps in this approach included Sonogashira coupling, Tsuji-Wacker oxidation, Evans-Saksena's 1,3--reduction, and Narasaka-Prasad's 1,3--reduction. The synthetic results unambiguously confirmed the absolute configuration of the natural products mucorisocoumarins A and B as (-)-(10,12)- and (+)-(10,12)-, respectively.
已完成从共同中间体（-）-6--甲基-香豆素（）到（-）-柠檬异香豆素（）、（-）柠檬异香豆醇（）、12--柠檬异香豆醇（）和（-）-粘霉素异香豆素 A () 和 B () 的 (-)-统一简洁的首次不对称全合成。该合成方法的核心是一种区域选择性的金（I）催化 6--环化策略，用于构建异香豆素骨架。该方法中的其他关键步骤包括 Sonogashira 偶联、Tsuji-Wacker 氧化、Evans-Saksena 的 1,3--还原和 Narasaka-Prasad 的 1,3--还原。合成结果明确证实了天然产物粘霉素异香豆素 A 和 B 的绝对构型分别为 (-)-(10,12)-和 (+)-(10,12)-。
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