Total Synthesis of the Proposed Microcyclamides MZ602 and MZ568
文献类型：期刊论文
| 作者 | Liu, Yi; Zhao, Xiangyun; Wang, Hongbo; Liu, Huili; Sui, Zhuyin; Yan, Bingfei; Du, Yuguo |
| 刊名 | JOURNAL OF ORGANIC CHEMISTRY
 |
| 出版日期 | 2021 |
| 卷号 | 86期号:1页码:1065-1073 |
| ISSN号 | 0022-3263 |
| 英文摘要 | The first convergent total synthesis for the proposed structures of microcyclamides MZ602 (1) and MZ568 (2) has been accomplished in 11 linear steps with 12.5 and 16.8% overall yield, respectively. Key features of the syntheses include a one-pot cascade reaction to construct core Boc-L-Ile-Thz-OAllyl fragment 5, and a removable pseudoproline (Psi(Me,Me) pro) inducer assisted cyclization of thiazole-containing all-L linear peptides. The spectral data (H-1 NMR, C-13 NMR, and HRMS) of synthetic MZ602 (1) were quite similar to those of the proposed natural microcyclamide MZ602, except to an opposite sign of the optical rotation value. Surprisingly, the synthetic MZ568 (2) presented large discrepancies in characteristic spectral data from those of the reported natural product, although the absolute configuration of key intermediate 36 was unambiguously determined by single-crystal X-ray analysis in our work. These findings revealed that the proposed structures of natural microcyclamides MZ602 and MZ568 required revision. |
| WOS研究方向 | Chemistry, Organic |
| 源URL | [http://ir.rcees.ac.cn/handle/311016/45863]  |
| 专题 | 生态环境研究中心_环境化学与生态毒理学国家重点实验室 |
| 作者单位 | 1.Yantai Univ, Key Lab Mol Pharmacol & Drug Evaluat, Minist Educ, Yantai 264005, Peoples R China 2.Chinese Acad Sci, Res Ctr Ecoenvironm Sci, State Key Lab Environm Chem & Ecotoxicol, Beijing 100085, Peoples R China 3.Yantai Univ, Sch Chem & Chem Engn, Yantai 264005, Peoples R China |
| 推荐引用方式 GB/T 7714 | Liu, Yi,Zhao, Xiangyun,Wang, Hongbo,et al. Total Synthesis of the Proposed Microcyclamides MZ602 and MZ568[J]. JOURNAL OF ORGANIC CHEMISTRY,2021,86(1):1065-1073. |
| APA | Liu, Yi.,Zhao, Xiangyun.,Wang, Hongbo.,Liu, Huili.,Sui, Zhuyin.,...&Du, Yuguo.(2021).Total Synthesis of the Proposed Microcyclamides MZ602 and MZ568.JOURNAL OF ORGANIC CHEMISTRY,86(1),1065-1073. |
| MLA | Liu, Yi,et al."Total Synthesis of the Proposed Microcyclamides MZ602 and MZ568".JOURNAL OF ORGANIC CHEMISTRY 86.1(2021):1065-1073. |
入库方式： OAI收割
来源：生态环境研究中心
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