Enantioselective Total Syntheses of Manginoids A and C and Guignardones A and C
Enantioselective Total Syntheses of Manginoids A and C and Guignardones A and C
复制标题
Manginoids A 和 C 以及 Guignardones A 和 C 的对映选择性全合成
DOI：
10.1002/anie.202104182
复制
发表时间：
2021
期刊：
影响因子：
--
通讯作者：
Lou Hong-Xiang
中科院分区：
文献类型：
--
作者：
Zong Yan;Xu Ze-Jun;Zhu Rong-Xiu;Su Ai-Hong;Liu Xu-Yuan;Zhu Ming-Zhu;Han Jing-Jing;Zhang Jiao-Zhen;Xu Yu-Liang;Lou Hong-Xiang
报道了一种对映选择性合成方法，制备了两种生物遗传学相关的萜类化合物——类曼碱和桂皮酮。这种生物启发和发散合成采用氧化1,3 -二羰基自由基引发的环化和共同前体的环脱水，在后期分别形成了类曼碱和桂皮酮的中心环。关键的合成步骤包括硅胶促进的半平纳醇重排形成6 -恶比环[3.2.1]辛烷骨架和溴乙烯的Suzuki-Miyaura反应实现片段偶联。该合成方案能够从市售材料中不对称合成四种真菌美罗萜类化合物。
An enantioselective synthetic approach for preparing manginoids and guignardones, two types of biogenetically related meroterpenoids, is reported. This bioinspired and divergent synthesis employs an oxidative 1,3‐dicarbonyl radical‐initiated cyclization and cyclodehydration of the common precursor to forge the central ring of the manginoids and guignardones, respectively, at a late stage. Key synthetic steps include silica‐gel‐promoted semipinacol rearrangement to form the 6‐oxabicyclo[3.2.1]octane skeleton and the Suzuki–Miyaura reaction of vinyl bromide to achieve fragment coupling. This synthesis protocol enables the asymmetric syntheses of four fungal meroterpenoids from commercially available materials.