一锅分步法全合成(+)-乙酰胆碱酯醇和(+)-7′，8′-二氢乙酰胆碱酯醇

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-03-20 DOI:10.1021/acs.orglett.5c00484

Atsushi Nakayama, Hidemitsu Yamanaka, Rika Yamasaki, Naoki Hashimoto, Tetsuro Shinada

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引用次数: 0

摘要

（+）-Aigialospirol和(+)-7′，8′-二氢aigialospirol是从红树源真菌Aigialus parvus BCC 5311中分离出来的螺旋酮型聚酮类天然产物。这些聚酮的结构特征是融合间环酸内酯和螺旋酮，其中含有六个不对称碳中心。在本文中，我们描述了基于生物合成启发转化的简明和立体选择性合成这些天然产物的九个步骤。全合成的重点是一锅逐步合成，包括(i)由手性环氧化物形成立体选择性内酯环，（ii）炔烃还原，（iii）全局去保护和（iv）螺旋酮形成，这些都是在全合成的最后一步进行的。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Total Syntheses of (+)-Aigialospirol and (+)-7′,8′-Dihydroaigialospirol by a One-Pot Stepwise Approach

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Total Syntheses of (+)-Aigialospirol and (+)-7′,8′-Dihydroaigialospirol by a One-Pot Stepwise Approach

(+)-Aigialospirol and (+)-7′,8′-dihydroaigialospirol are known to be spiroketal polyketide-type natural products isolated from mangrove-derived fungus Aigialus parvus BCC 5311. These polyketides are structurally characterized by fusing resorcylic acid lactone and spiroketal moieties containing six asymmetric carbon centers. In this paper, we describe concise and stereoselective syntheses of these natural products based on biosynthesis-inspired transformation in nine steps. The total syntheses are highlighted by a one-pot stepwise synthesis involving (i) stereoselective lactone ring formation from a chiral epoxide, (ii) reduction of alkyne, (iii) global deprotection, and (iv) spiroketal formation, which are performed in the final step of the total synthesis.

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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.