An Approach toward 17-Arylsubstituted Marginatafuran-Type Isospongian Diterpenoids via a Palladium-Catalyzed Heck–Suzuki Cascade Reaction of 16-Bromolambertianic Acid Научная публикация
| Журнал |
Molecules
, E-ISSN: 1420-3049 |
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| Вых. Данные | Год: 2022, Том: 27, Номер: 9, Страницы: 2643 Страниц : 1 DOI: 10.3390/molecules27092643 | ||
| Ключевые слова | isospongian-type diterpenes; furanolabdanoids; lambertianic acid; palladium-catalyzed Heck–Suzuki cascade reaction; diastereoselectivity | ||
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Реферат:
Isospongian diterpenes are a small but growing family of natural tetracyclic secondary metabolites isolated from marine organisms, primarily sponges and nudibranchs. A palladium-catalyzed domino Heck–Suzuki reaction sequence for the synthesis of the tetracyclic skeleton of marginatafuran-type isospongian diterpenoids with a wide variety of substituents in the C-17 position is reported. The proposed approach was based on selective transformations of the accessible plant diterpenoid lambertianic acid and includes an intramolecular Heck reaction of 16-bromolambertianic and arylation of the palladium intermediate with arylboronic acid. The influence of the nature of the substituent both in arylboronic acids and in the furan ring of 16-bromolambertianic acid on the direction and chemoselectivity of the reaction has been studied. The described derivatization of natural furanolabdanoid lambertianic acid produced new functionalized molecules for biological study and gave novel insights into the reactivity of complex molecular structures.
Библиографическая ссылка:
Kharitonov Y.V.
, Shults E.E.
An Approach toward 17-Arylsubstituted Marginatafuran-Type Isospongian Diterpenoids via a Palladium-Catalyzed Heck–Suzuki Cascade Reaction of 16-Bromolambertianic Acid
Molecules. 2022. V.27. N9. P.2643. DOI: 10.3390/molecules27092643 WOS РИНЦ OpenAlex
An Approach toward 17-Arylsubstituted Marginatafuran-Type Isospongian Diterpenoids via a Palladium-Catalyzed Heck–Suzuki Cascade Reaction of 16-Bromolambertianic Acid
Molecules. 2022. V.27. N9. P.2643. DOI: 10.3390/molecules27092643 WOS РИНЦ OpenAlex
Даты:
| Поступила в редакцию: | 30 мар. 2022 г. |
| Принята к публикации: | 19 апр. 2022 г. |
| Опубликована online: | 20 апр. 2022 г. |
Идентификаторы БД:
| Web of science: | WOS:000794514600001 |
| РИНЦ: | 48581616 |
| OpenAlex: | W4224283168 |