Synthesis of Leiodolide A Macrolactone

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-03-06 DOI:10.1021/acs.orglett.5c00209

David R. Williams, Fese M. Okha, Sarah A. Ward

引用次数: 0

Abstract

A convergent route toward the synthesis of leiodolide A (1) is described. Our studies explored reactions of the indium chloride-induced transmetalation of allylic stannane 32 for nucleophilic addition with nonracemic aldehyde 15. The stereoselective formation of the all-syn stereotriad was rationalized by an in situ isomerization to produce the Z-allylindium reagent for subsequent anti-Felkin addition. The inversion of C₁₇ stereochemistry led to an effective π-allyl Stille cross coupling utilizing Z-alkenylstannane 11b. The Horner–Wadsworth–Emmons reaction provides macrolactone 37 which exhibits discrepancies as compared with reported NMR data for the purported leiodolide A.

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列碘内酯A大内酯的合成

介绍了一种合成碘素A(1)的收敛路线。我们的研究探讨了氯化铟诱导烯丙基锡烷32与非外消旋醛15的亲核加成反应。通过原位异构化使全同步立体三联体的立体选择性形成合理化，从而产生后续抗费金加成的z -烯丙基lindium试剂。C17立体化学的反转导致了z -烯基锡烷11b有效的π-烯丙基Stille交叉偶联。Horner-Wadsworth-Emmons反应提供了大内酯37，与报道的leiodolide A的核磁共振数据相比，显示出差异。

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.