Synthesis of Leiodolide A Macrolactone

IF 4.9 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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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.