Synthetic transformations of higher terpenoids. XXVII.* Synthesis of 7-hydroxylabdanoids and their transformations

Synthetic transformations of higher terpenoids. XXVII.* Synthesis of 7-hydroxylabdanoids and their transformations Full article

Journal

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

Output data

Year: 2012, Volume: 48, Number: 2, Pages: 250-257 Pages count : DOI: 10.1007/s10600-012-0215-3

Tags

phlomisoic acid; synthesis; 7R-hydroxy-15,16-epoxy-8(9),13(16),14-labdatrien-18-oic acid; 7-ketolabdanoids; oximes; 5-furan-3-ylethylbenzoazepines; XSA

Authors

Kharitonov Yu V. ¹ , Shul'ts E. E. ¹ , Gatilov Yu V. ¹ , Bagryanskaya I. Yu ¹ , Shakirov M. M. ¹ , Tolstikov G. A. ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Novosibirsk 630090, Russia

Allylic oxidation of phlomisoic acid and its methyl ester by selenium dioxide occurred stereoselectively to form 7 alpha-hydroxy derivatives of labdanoids, which were oxidized by active manganese dioxide to 7-ketofuranolabdanoids. Oximation of the last by hydroxylamine hydrochloride in MeOH in the presence of NaOAc gave pure (E)-ketooximes. Beckmann rearrangement of 7-ketooximes of phlomisoic acid and its methyl ester occurred with formation of the corresponding octahydro-1 H-benzoazepines.

Kharitonov Y.V. , Shul'ts E.E. , Gatilov Y.V. , Bagryanskaya I.Y. , Shakirov M.M. , Tolstikov G.A.
Synthetic transformations of higher terpenoids. XXVII.* Synthesis of 7-hydroxylabdanoids and their transformations
Chemistry of Natural Compounds. 2012. V.48. N2. P.250-257. DOI: 10.1007/s10600-012-0215-3 WOS Scopus РИНЦ

Published print:	May 1, 2012
Published online:	May 16, 2012

Web of science	WOS:000304651800018
Scopus	2-s2.0-85027930101
Elibrary	41780173
OpenAlex	W2038441877