海洋多酮类化合物 Plakortone Q 的全合成

IF 1.5 4区医学 Q4 CHEMISTRY, MEDICINAL

Chemical & pharmaceutical bulletin Pub Date : 2024-02-03 DOI:10.1248/cpb.c23-00876

Shinnosuke Okazaki, Kaho Senda, Ayaka Tokuta, Misa Inagaki, Kazuo Kamaike, Koichiro Ota, Hiroaki Miyaoka

引用次数: 0

摘要

以(R)-罗氏酯为原料，通过 24 个步骤实现了天然双环[3.3.0]呋喃内酯多酮--plakortone Q 的全合成。该合成策略的主要特点是通过对环氧乙烷取代的烯烃进行 Upjohn 二羟基化和酸介导的 5-endo-tet 环化反应，立体选择性地构建了一个具有四个连续立体异构中心的四氢呋喃中心分子。

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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Total Synthesis of Marine Polyketide Plakortone Q

The total synthesis of the natural bicyclo[3.3.0]furanolactone polyketide, plakortone Q, was achieved in 24 steps from (R)-Roche ester. The main feature of this synthetic strategy is the stereoselective construction of a central tetrahydrofuran moiety with four consecutive stereoisomeric centers using the Upjohn dihydroxylation of oxiranyl-substituted alkenes and acid-mediated 5-endo-tet cyclization.

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来源期刊

Chemical & pharmaceutical bulletin 医学-化学综合

CiteScore

3.20

自引率

5.90%

发文量

132

审稿时长

1.7 months

期刊介绍： The CPB covers various chemical topics in the pharmaceutical and health sciences fields dealing with biologically active compounds, natural products, and medicines, while BPB deals with a wide range of biological topics in the pharmaceutical and health sciences fields including scientific research from basic to clinical studies. For details of their respective scopes, please refer to the submission topic categories below. Topics: Organic chemistry In silico science Inorganic chemistry Pharmacognosy Health statistics Forensic science Biochemistry Pharmacology Pharmaceutical care and science Medicinal chemistry Analytical chemistry Physical pharmacy Natural product chemistry Toxicology Environmental science Molecular and cellular biology Biopharmacy and pharmacokinetics Pharmaceutical education Chemical biology Physical chemistry Pharmaceutical engineering Epidemiology Hygiene Regulatory science Immunology and microbiology Clinical pharmacy Miscellaneous.