Synthetic transformations of higher terpenoids: XXII. Reactions of lambertianic acid derivatives with organozinc reagents obtained from ethyl bromoalkanoates

Synthetic transformations of higher terpenoids: XXII. Reactions of lambertianic acid derivatives with organozinc reagents obtained from ethyl bromoalkanoates Full article

Journal

Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393

Output data

Year: 2010, Volume: 46, Number: 9, Pages: 1339-1347 Pages count : 9 DOI: 10.1134/S1070428010090137

Authors

Kharitonov Yu V. ¹ , Shults E.E. ¹ , Shakirov M.M. ¹ , Bagryanskaya I.Yu ¹ , Tolstikov G.A. ¹

Affiliations

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

Reactions of 16-cyanomethyllambertianate with organozinc reagents obtained from ethyl esters of alpha-bromoacetic, alpha-bromopropionic, and alpha-bromobutyric acids gave the corresponding enaminoesters, beta-ketoesters, and beta-hydroxyesters of labdanoids whose yield depended on the reaction conditions and the structure of the alpha-bromoester. By Reformatsky reaction of 16-formylmethyllambertianate with alpha-bromoesters of carboxylic acids stereoisomeric beta-hydroxyesters of labdanoids were synthesized.

Kharitonov Y.V. , Shults E.E. , Shakirov M.M. , Bagryanskaya I.Y. , Tolstikov G.A.
Synthetic transformations of higher terpenoids: XXII. Reactions of lambertianic acid derivatives with organozinc reagents obtained from ethyl bromoalkanoates
Russian Journal of Organic Chemistry. 2010. V.46. N9. P.1339-1347. DOI: 10.1134/S1070428010090137 WOS Scopus РИНЦ

Published print:	Sep 1, 2010
Published online:	Oct 19, 2010

Web of science	WOS:000283147600013
Scopus	2-s2.0-77958503778
Elibrary	16698397
OpenAlex	W2028036251