Asymmetric Total Synthesis of Eremophilanolide Sesquiterpene Xylareremophil and Its Congeners

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-02-24 DOI:10.1021/acs.orglett.5c00028

Hui-Bin Wang, Tian-Jie Ge, Xian-Tao An, Xin-Yu Liu, Le-Le Meng, Yu-Han Yang, Jun-Yi Zhou, Xian-He Zhao, Chun-An Fan

引用次数: 0

Abstract

The first asymmetric, protecting group free total synthesis of eremophilanolide sesquiterpenes, xylareremophil (1), 2α,3α-epoxymairetolide A (2), and 2,3-seco-2,3-olide-1-deoxygenmairetolide F (3), is concisely achieved with a longest linear route of five to eight steps, starting from the known (5S)-5,6-dimethyl-2-cyclohexenone as the chiral starting material. This synthetic approach mainly features an oxa-Pauson–Khand reaction of the highly functionalized chiral aldehyde precursor, forging a γ-butenolide-fused tricyclic core framework of eremophilanolides in a one-step manner. This study provides a novel strategic perspective for the divergent synthesis of the eremophilanolide sesquiterpenes.

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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.