水蚤丙足碱的合成研究

IF 5 1区 化学 Q1 CHEMISTRY, ORGANIC
Hai-Kang Mao, Qian Wang, Sujun Xie and Jing Xu*, 
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引用次数: 0

摘要

Daphnimacropodines A-C 是 Daphniphyllum 生物碱亚家族中一个小而结构独特的成员。它们拥挤的多环骨架和两个邻接的季基立体中心给合成带来了巨大挑战。本文介绍了两种立体选择性方法,利用简单的构建模块,通过直接的 Rh 催化 [4 + 3] 环加成反应,构建出水飞蓟宾的三环核心结构。这项研究还重点介绍了快速组装环己烷环分子的分子内 Heck 反应、锻造关键 C-8 季立体中心的 Tsuji-Trost 烯丙基化反应、高效的杂 Diels-Alder 反应以及为关键环戊烷环铺平道路的分子内亲核加成反应。此外,还研究了四氢吡咯基团的组装。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Synthetic Study toward Daphnimacropodines

Synthetic Study toward Daphnimacropodines

Daphnimacropodines A-C are members of a small but structurally distinct subfamily of Daphniphyllum alkaloids. Their congested polycyclic skeletons, and two vicinal quaternary stereocenters, present significant synthetic challenges. This paper describes two stereoselective approaches to constructing the tricyclic core structures of daphnimacropodines, achieved through a straightforward Rh-catalyzed [4 + 3] cycloaddition using simple building blocks. This work also highlights an intramolecular Heck reaction that rapidly assembles the cyclohexane ring moiety, a Tsuji-Trost allylation that forged the critical C-8 quaternary stereocenter, an efficient hetero-Diels–Alder reaction, and an intramolecular nucleophilic addition, which paved the way to the key cyclopentane ring. The assembly of the tetrahydropyrrole motif was also investigated.

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来源期刊
Organic Letters
Organic Letters 化学-有机化学
CiteScore
9.30
自引率
11.50%
发文量
1607
审稿时长
1.5 months
期刊介绍: Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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