A synthetic investigation into the biosynthesis of hypsampsone A†

IF 2.7 3区化学 Q1 CHEMISTRY, ORGANIC

Organic & Biomolecular Chemistry Pub Date : 2025-04-08 DOI:10.1039/d5ob00045a

Jhayden J. A. Jarman , Andreas B. zur Bonsen , Jonathan H. George

引用次数: 0

Abstract

A simplified proposal for the biogenetic origin of hypsampsone A, a complex meroterpenoid, is supported by a bioinspired cascade reaction that rapidly assembles its polycyclic core. The key steps in both the proposed biosynthesis and the bioinspired cascade are a spontaneous intramolecular carbonyl–ene reaction, an α-hydroxy-β-diketone rearrangement and a terminating intramolecular aldol reaction. The feasibility of this model cascade reaction strongly suggests that hypsampsone A is a highly rearranged member of the polycyclic polyprenylated acylphloroglucinol (PPAP) family of natural products.

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hypsampsone A†的生物合成研究

hypsampsone A是一种复杂的巯基萜类化合物，其生物遗传学起源的简化建议得到了生物启发级联反应的支持，该反应可快速组装其多环核心。提出的生物合成和生物启发级联的关键步骤是自发的分子内羰基烯反应，α-羟基-β-二酮重排和分子内终止醛醇反应。该模型级联反应的可行性强烈表明，hypsampsone A是天然产物多环聚丙烯酰化酰基间苯三酚（PPAP）家族的高度重排成员。

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 & Biomolecular Chemistry 化学-有机化学

CiteScore

5.50

自引率

9.40%

发文量

1056

审稿时长

1.3 months

期刊介绍： Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.