Total Syntheses of Daphenylline, Daphnipaxianine A, and Himalenine D

被引：98
|
作者：
Chen, Yu [1 ]
Zhang, Wenhao [1 ]
Ren, Lu [1 ]
Li, Jian [1 ]
Li, Ang [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Collaborat Innovat Ctr Chem Life Sci, State Key Lab Bioorgan & Nat Prod Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 04期
基金：
中国国家自然科学基金;
关键词：
alkaloids; arene synthesis; bioinspired synthesis; cascade reactions; 3+2] cycloaddition; ELECTRON-DEFICIENT OLEFINS; BIOMIMETIC TOTAL-SYNTHESIS; DAPHNIPHYLLUM ALKALOIDS; CONSTRUCTION; CHEMISTRY; CYCLOADDITION; SKELETON; CORE;
D O I：
10.1002/anie.201711482
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We report the total syntheses of daphenylline (1), daphnipaxianine A (5), and himalenine D (6), three Daphniphyllum alkaloids from the calyciphylline A subfamily. A pentacyclic triketone was prepared by using atom-transfer radical cyclization and the Lu [3+2] cycloaddition as key steps. Inspired by the proposed biosynthetic relationship between 1 and another calyciphylline A type alkaloid, we developed a ring-expansion/aromatization/aldol cascade to construct the tetrasubstituted benzene moiety of 1. The versatile triketone intermediate was also elaborated into 5 and 6 through a C=C bond migration/aldol cyclization approach.
引用
收藏
页码：952 / 956
页数：5
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