Synthetic Studies of Zoaramine: Construction of the Tetracyclic Skeleton in High Oxidation State

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-03-03 DOI:10.1021/acs.orglett.4c04662

Guoen Wen, Shuo Gu, Jie Chen, Haibing He, Shuanhu Gao

引用次数: 0

Abstract

We report herein the synthetic studies toward zoaramine, a member of the family of zoaramine-type marine natural products bearing a unique structure. The major synthetic challenge is the stereoselective construction of the congested tetracyclic [6–6–6–6] skeleton in a high oxidation state. Our key strategies are the following: (1) radical cyclization was designed to install the quaternary stereocenters at C-9, C-22, and C-12 as well as formation of the B and D rings; (2) selective oxidations were realized to introduce the functional groups at C-11 and C-24 by using O₂/t-BuOK-promoted hydroxylation and MeReO₃-catalyzed Rubottom oxidation. Our studies reveal a special reactivity and stereocontrol model in the specific chemical environments, which might benefit the related synthetic exploration of this family of natural alkaloids.

Abstract Image

查看原文本刊更多论文

求助全文

约1分钟内获得全文求助全文

来源期刊

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.