Synthetic transformations of higher terpenoids: XIX. Synthesis of 1,7-epoxyisoindolones and 7,9a-epoxythiazolo[2,3-a]isoindolones from terpenoids

Synthetic transformations of higher terpenoids: XIX. Synthesis of 1,7-epoxyisoindolones and 7,9a-epoxythiazolo[2,3-a]isoindolones from terpenoids Full article

Journal

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

Output data

Year: 2009, Volume: 45, Number: 5, Pages: 637-649 Pages count : 13 DOI: 10.1134/S1070428009050017

Authors

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

Affiliations

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

The reductive amination of methyl 16-formyllambertianate with L-leucine or L-methionine esters resulted in labdanoid furfurylamines whose acylation with maleic anhydride on chlorides of methacrylic or crotonic acids gave the corresponding unsaturated amides that readily entered into the reaction of intramolecular [4+2]-cycloaddition giving the corresponding derivatives of 10-oxa-3-azatricyclo[5.2.1.0(1,5)]dec-8-en-4-one. As a result of a sequence of reactions: The amination of methyl 16-formyllambertianate with cystamine, the acylation of the obtained methyl 16-thiazolidinyllambertianate with the above mentioned acid chlorides or with maleic anhydride, and the intramolecular cyclization of the arising furfurylamine we obtained terpenoid derivayives of 7,9a-epoxyhexahydrothiazolo[2,3-a]isoindol-5-one.

Kharitonov Y.V. , Shults E.E. , Shakirov M.M. , Tolstikov G.A.
Synthetic transformations of higher terpenoids: XIX. Synthesis of 1,7-epoxyisoindolones and 7,9a-epoxythiazolo[2,3-a]isoindolones from terpenoids
Russian Journal of Organic Chemistry. 2009. V.45. N5. P.637-649. DOI: 10.1134/S1070428009050017 WOS Scopus РИНЦ

Published print:	May 1, 2009
Published online:	Jun 9, 2009

Web of science	WOS:000266829300001
Scopus	2-s2.0-67049132873
Elibrary	13604322
OpenAlex	W2008985315