Total Syntheses of Daphenylline, Daphnipaxianine A, and Himalenine D

被引：115

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

页码：952 / 956

页数：5

共 56 条

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