Synthetic Transformations of Higher Terpenoids. XXXIII. Preparation of 15,16-Dihydroisopimaric Acid and Methyl Dihydroisopimarate and their Transformations Научная публикация
| Журнал |
Chemistry of Natural Compounds
ISSN: 0009-3130 , E-ISSN: 1573-8388 |
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| Вых. Данные | Год: 2014, Том: 49, Номер: 6, Страницы: 1067-1075 Страниц : DOI: 10.1007/s10600-014-0823-1 | ||
| Ключевые слова | tricyclic diterpenoids; 15,16-dihydroisopimaric acid; isolation; oxidation; 7-hydroxy-derivatives; 14-hydroxy-derivatives; oximes; Beckmann rearrangement | ||
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Реферат:
Methods were proposed for preparing 15,16-dihydroisopimaric acid and its methyl ester. Oxidation of methyl dihydroisopimarate through the action of 3-chloroperbenzoic acid occurred with formation of 7,8-epoxy-derivatives and 7 alpha-hydroxydihydrosandaracopimarate. The latter in addition to 7-oxotetrahydroisopimarate were formed through the action of t-butylhydroperoxide in the presence of MoCl5. Oxidation of dihydroisopimaric acid or the ester by selenium dioxide in dioxane gave the corresponding 14 alpha-hydroxy-derivatives. Pyridinium chlorochromate transformed 14 alpha-hydroxydihydroisopimarate into a mixture of methyl esters of 7 alpha-hydroxy-8,14-epoxyisopimaric, 7-oxo-8,14-epoxyisopimaric, 7-oxo-14-hydroxyisopimaric, and 7 alpha-hydroxysandaracopimaric acids. Oximation of methyl 7-oxotetrahydroisopimarate by hydroxylamine hydrochloride in MeOH in the presence of NaOAc gave a mixture of the corresponding (Z)- and (E)-oximes. Beckmann rearrangement of the 7-(E)-oxime of methyl tetrahydroisopimarate through the action of thionylchloride led to tetradecahydrodibenzo[b,d]azepine.
Библиографическая ссылка:
Kharitonov Y.V.
, Shul'ts E.E.
, Shakirov M.M.
Synthetic Transformations of Higher Terpenoids. XXXIII. Preparation of 15,16-Dihydroisopimaric Acid and Methyl Dihydroisopimarate and their Transformations
Chemistry of Natural Compounds. 2014. V.49. N6. P.1067-1075. DOI: 10.1007/s10600-014-0823-1 WOS Scopus РИНЦ OpenAlex
Synthetic Transformations of Higher Terpenoids. XXXIII. Preparation of 15,16-Dihydroisopimaric Acid and Methyl Dihydroisopimarate and their Transformations
Chemistry of Natural Compounds. 2014. V.49. N6. P.1067-1075. DOI: 10.1007/s10600-014-0823-1 WOS Scopus РИНЦ OpenAlex
Даты:
| Опубликована в печати: | 1 янв. 2014 г. |
| Опубликована online: | 12 янв. 2014 г. |
Идентификаторы БД:
| Web of science: | WOS:000330713200018 |
| Scopus: | 2-s2.0-84894061142 |
| РИНЦ: | 21865679 |
| OpenAlex: | W2012617031 |