Synthetic Studies on Tricyclic Diterpenoids: Direct Allylic Amination Reaction of Isopimaric Acid Derivatives

Synthetic Studies on Tricyclic Diterpenoids: Direct Allylic Amination Reaction of Isopimaric Acid Derivatives Научная публикация

Журнал

ChemistryOpen
ISSN: 2191-1363

Вых. Данные

Год: 2016, Том: 5, Номер: 1, Страницы: 65-70 Страниц : 6 DOI: 10.1002/open.201500187

Ключевые слова

allylic amination reaction; diterpenoids; gold catalysis; pimaranes; stereoselectivity

Авторы

Timoshenko Mariya A. ^1,2,3 , Kharitonov Yurii V. ^1,2,3 , Shakirov Makhmut M. ¹ , Bagryanskaya Irina Yu. ^1,2,3 , Shults Elvira E. ^1,2,3

Организации

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, Novosibirsk Inst Organ Chem, Med Chem Lab, Lavrentyev Ave 9, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Dept Chem, Pirogova St 2, Novosibirsk 630090, Russia
3	(Данные Web of science) Novosibirsk State Univ, Dept Phys, Pirogova St 2, Novosibirsk 630090, Russia

A selective synthesis of 7- or 14-nitrogen containing tricyclic diterpenoids was completed according to a strategy in which the key step was the catalyzed direct allylic amination of methyl 14-hydroxy-15,16-dihydroisopimarate with a wide variety of nitrogenated nucleophiles. It was revealed that the selectivity of the reaction depends on the nature of nucleophile. The catalyzed reaction of the mentioned diterpenoid allylic alcohol with 3-nitroaniline, 3-(trifluoromethyl)aniline, and 4-(trifluoromethyl)aniline yield the subsequent 7-, 7- and 14nitrogen-containing diterpenoids. The reaction with 2-nitroaniline, 4-nitro-2-chloroaniline, 4-methoxy-2-nitroaniline, phenylsulfamide, or tert-butyl carbamate proceeds with the formation of 7-nitrogen-substituted diterpenoids as the main products.

Timoshenko M.A. , Kharitonov Y.V. , Shakirov M.M. , Bagryanskaya I.Y. , Shults E.E.
Synthetic Studies on Tricyclic Diterpenoids: Direct Allylic Amination Reaction of Isopimaric Acid Derivatives

ChemistryOpen. 2016. V.5. N1. P.65-70. DOI: 10.1002/open.201500187 WOS Scopus

Полный текст от издателя

Опубликована online:	28 окт. 2015 г.
Опубликована в печати:	1 февр. 2016 г.

Web of science	WOS:000370451400009
Scopus	2-s2.0-84959545685
OpenAlex	W2220913190