通过环硼酯介导的非对映选择性烯基化，立体控制发散全合成(+)-7-脱氧葡萄树汀、(+)-7-脱氧反式二氢精氨酸和(+)-石蒜碱。

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-10-09 DOI:10.1021/acs.orglett.5c03530

Heesun Yu,Hyoungsu Kim,Dongjoo Lee

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引用次数: 0

摘要

通过对一种常见的后期中间体的C(1)羟基的操纵，实现了立体控制发散式全合成的Amaryllidaceae异碳苯乙烯类生物碱。该合成的主要特征包括：(1)环硼酯介导的非对映选择性烯基化，用于早期安装C（10b）立体中心；(2)螯合控制的立体选择性同位烯丙基化，用于设置C(2)立体中心；(3)n- boc -叠氮啶的罕见区域和立体选择性打开，然后消除以构建烯丙基胺部分。

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Stereocontrolled Divergent Total Syntheses of (+)-7-Deoxypancratistatin, (+)-7-Deoxy-trans-dihydronarciclasine, and (+)-Lycoricidine via Cyclic Boronic Ester-Mediated Diastereoselective Alkenylation.

Stereocontrolled divergent total syntheses of Amaryllidaceae isocarbostyril alkaloids have been accomplished through the manipulation of the C(1) hydroxyl group from a common late-stage intermediate. Key features of the synthesis include (1) a cyclic boronic ester-mediated diastereoselective alkenylation for an early stage installation of the C(10b) stereocenter, (2) a chelation-controlled stereoselective syn-allylation to set the C(2) stereocenter, and (3) a rare regio- and stereoselective opening of N-Boc-aziridine followed by elimination to construct the allylic amine moiety.

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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.