Efficient Synthesis of the N-(buta-2,3-dienyl)carboxamide of Isopimaric Acid and the Potential of This Compound towards Heterocyclic Derivatives of Diterpenoids

Efficient Synthesis of the N-(buta-2,3-dienyl)carboxamide of Isopimaric Acid and the Potential of This Compound towards Heterocyclic Derivatives of Diterpenoids Научная публикация

Журнал

ChemistryOpen
ISSN: 2191-1363

Вых. Данные

Год: 2018, Том: 7, Номер: 11, Страницы: 890-901 Страниц : 12 DOI: 10.1002/open.201800205

Ключевые слова

chromenes; cross-coupling; cyclization; heterocycles; terpenoids

Авторы

Gromova Marya A. ¹ , Kharitonov Yurii, V ¹ , Bagryanskaya Irina Yu ^2,3 , Shults Elvira E. ^1,3

Организации

1	(Данные Web of science) Novosibirsk Inst Organ Chem SB RAS, Lavrentjev Ave 9, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk Inst Organ Chem SB RAS, Dept Phys Chem, Lavrentjev Ave 9, Novosibirsk 630090, Russia
3	(Данные Web of science) Novosibirsk State Univ, Pirogova St 2, Novosibirsk 630090, Russia

The N-(2,3-butadienyl)carboxamide of isopimaric acid, that is, compound 3, was prepared through a two-step synthetic procedure starting from the natural diterpene isopimaric acid. The Pd-catalyzed cross-coupling and subsequent cyclization of terpenoid allene 3 with several aryl iodides and aryl bromides gave access to optically active diterpenoid-oxazoline derivatives in good to excellent yields. The functional group tolerance in the aryl iodides was demonstrated by several examples, including substrates with additional N-tert-butoxycarbonyl-protected amino, hydroxy, and carboxy substituents in the ortho position. The cross-coupling-cyclization reaction of those compounds with allene 3 proceeded selectively with the formation of cyclization products on the substituent in the aromatic ring. This transformation opens a potential route to the synthesis of hybrid compounds containing a tricyclic diterpenoid and several heterocycles.

Gromova M.A. , Kharitonov Y.V. , Bagryanskaya I.Y. , Shults E.E.
Efficient Synthesis of the N-(buta-2,3-dienyl)carboxamide of Isopimaric Acid and the Potential of This Compound towards Heterocyclic Derivatives of Diterpenoids

ChemistryOpen. 2018. V.7. N11. P.890-901. DOI: 10.1002/open.201800205 WOS Scopus РИНЦ OpenAlex

Полный текст от издателя

Опубликована в печати:	1 нояб. 2018 г.
Опубликована online:	14 нояб. 2018 г.

Web of science:	WOS:000451837300007
Scopus:	2-s2.0-85057541553
РИНЦ:	38619518
OpenAlex:	W2901977736

БД	Цитирований
Web of science	5
Scopus	7
РИНЦ	7
OpenAlex	9