新霉素B螺旋酮亚基的快速合成：单端异头螺旋酮的立体化学性质及立体中心重配的建议

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-12-09 DOI:10.1021/acs.orglett.4c0375110.1021/acs.orglett.4c03751

Anna E. Healy, Marcus D. Van Engen, Nicholas A. Cinti and Paul E. Floreancig*,

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引用次数: 0

摘要

Neaumycin B 是一种复杂的多酮类化合物，对 U87 胶质母细胞瘤细胞具有惊人的细胞毒性。单个异构体螺酮核心是该天然产物结构中的一个重要亚基。我们报告了一种快速聚合螺酮基团的方法，其结果是形成了两种同分异构的单异构螺酮。我们描述了螺环形成过程中这一罕见结果的起源，随后提出了对天然产物中一个立体中心的修正。

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Rapid Synthesis of the Spiroketal Subunit of Neaumycin B: Stereochemical Aspects of Singly Anomeric Spiroketals and Proposal for a Stereocenter Reassignment

Neaumycin B is a complex polyketide that shows phenomenal cytotoxicity against U87 glioblastoma cells. The singly anomeric spiroketal core is a notable subunit in the natural product’s structure. We report a rapid and convergent approach to the spiroketal group, resulting in the formation of two isomeric singly anomeric spiroketals. We describe the origin of this rarely described outcome in spirocycle formation and subsequently propose a correction to a stereocenter in the natural product.

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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.