Synthetic Transformations of Higher Terpenoids. 38.* Synthesis of Conjugates Containing beta-Carboline and Tricyclic Diterpenoids

Synthetic Transformations of Higher Terpenoids. 38.* Synthesis of Conjugates Containing beta-Carboline and Tricyclic Diterpenoids Full article

Journal

Chemistry of Natural Compounds
ISSN: 0009-3130 , E-ISSN: 1573-8388

Output data

Year: 2019, Volume: 55, Number: 5, Pages: 871-877 Pages count : 7 DOI: 10.1007/s10600-019-02836-y

Tags

diterpenoids; isopimaric acid; beta-carbolines; heterocyclic compounds; Pictet-Spengler reaction; XSA

Authors

Gromova M.A. ¹ , Kharitonov Yu.V. ¹ , Rybalova T.V. ^1,2 , Shul'ts E.E. ^1,2

Affiliations

1	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, 9 Lavrenteva Prosp, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, 1 Pirogova St, Novosibirsk 630090, Russia

The synthesis and properties of tricyclic pimaranes containing a C-16 beta-carboline are reported. A Pictet-Spengler reaction of methyl 15-oxo-16-formylisopimarate (prepared in situ from the 15-oxo-15,16-dihydroisopimarate) and tryptamine or tryptophan methyl ester in the presence of trifluoroacetic acid formed a mixture of terpenoid 1,2,3,4-tetrahydro-beta-carbolines, 3,4-dihydro-beta-carbolines, and beta-carbolines. Tetrahydro- and dihydro-beta-carbolines in CHCl3 were oxidized to the corresponding beta-carbolines by treatment in air with basic Al2O3.

Gromova M.A. , Kharitonov Y.V. , Rybalova T.V. , Shul'ts E.E.
Synthetic Transformations of Higher Terpenoids. 38.* Synthesis of Conjugates Containing beta-Carboline and Tricyclic Diterpenoids
Chemistry of Natural Compounds. 2019. V.55. N5. P.871-877. DOI: 10.1007/s10600-019-02836-y WOS Scopus РИНЦ

Published print:	Sep 1, 2019
Published online:	Oct 11, 2019

Web of science	WOS:000496665100019
Scopus	2-s2.0-85074480854
Elibrary	41694910
OpenAlex	W2979912398