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

Journal ChemistryOpen
ISSN: 2191-1363
Output data Year: 2016, Volume: 5, Number: 1, Pages: 65-70 Pages count : 6 DOI: 10.1002/open.201500187
Tags allylic amination reaction; diterpenoids; gold catalysis; pimaranes; stereoselectivity
Authors 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
Affiliations
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

Abstract: 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.
Cite: 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
Files: Full text from publisher
Dates:
Published online: Oct 28, 2015
Published print: Feb 1, 2016
Identifiers:
Web of science WOS:000370451400009
Scopus 2-s2.0-84959545685
OpenAlex W2220913190
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