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Recent advances in the application of the isoxazoline route to aldols in the synthesis of natural products Обзор

Журнал Natural Product Reports
ISSN: 1460-4752
Вых. Данные Год: 2025, Том: 42, Страницы: 876-910 Страниц : 35 DOI: 10.1039/d4np00069b
Авторы Ushakov Pavel Yu. 1 , Sukhorukov Alexey Yu. 1
Организации
1 Laboratory of Organic and Metal-Organic Nitrogen-oxygen Systems, N. D. Zelinsky Institute of Organic Chemistry, Leninsky prospect, 47, Moscow, 119991, Russia

Реферат: The cycloaddition of nitrile oxides with olefins (NOC), followed by reductive cleavage of the resulting isoxazolines, has been widely recognised as a convenient and powerful synthetic strategy for constructing the aldol motif in natural product synthesis. Different modes of NOC (intermolecular, fused and bridged intramolecular) enable the synthesis of diverse isoxazoline products, which can be converted into highly substituted cyclic and acyclic aldol frameworks. This review examines the advances in this field over the past 25 years. More than 50 total syntheses are discussed, encompassing various classes of natural compounds, including macrolides, alkaloids, terpenoids, steroids, pseudosugars, sulfolipids and some others. Moreover, the basic aspects of this methodology are outlined, including methods for the generation of nitrile oxides and isoxazoline ring cleavage, as well as stereochemical models for intramolecular nitrile oxide cycloaddition.
Библиографическая ссылка: Ushakov P.Y. , Sukhorukov A.Y.
Recent advances in the application of the isoxazoline route to aldols in the synthesis of natural products
Natural Product Reports. 2025. V.42. P.876-910. DOI: 10.1039/d4np00069b WOS Scopus OpenAlex
Идентификаторы БД:
Web of science: WOS:001448561800001
Scopus: 2-s2.0-105000312218
OpenAlex: W4408649698
Цитирование в БД:
БД Цитирований
OpenAlex 6
Web of science 4
Scopus 3
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