Bioinspired Stereoselective Total Synthesis of the Caged Sesquiterpenoid Daphnepapytone A.

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-05-15 DOI:10.1021/acs.orglett.5c01509

Yan Zhang,Pengfei Yu,Wei Chen,Jia Li,Kai Liu,Xingang Xie,Huilin Li,Xuegong She

引用次数: 0

Abstract

The first total synthesis of the novel caged sesquiterpenoid daphnepapytone A is disclosed. Key reactions include a Pauson-Khand cycloaddition to provide oleodaphone, a bioinspired photoinduced [2 + 2] cycloaddition to forge the cyclobutane-containing caged skeleton, and a C-H oxidation and reduction protocol to generate daphnepapytone A. Finally, the 17-step synthetic sequence is shortened to 4 steps in protecting group-free and exclusively stereoselective fashion.

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笼型倍半萜烯甲酮A的生物激发立体选择性全合成。

公开了新型笼型倍半萜烯酮A的首次全合成。关键反应包括Pauson-Khand环加成生成油酮，生物激发光诱导[2 + 2]环加成生成含环丁烷的笼状骨架，C-H氧化还原生成纸浆酮a。最后，将17步合成序列缩短为4步，以保护无基团和完全立体选择的方式。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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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.