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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

Abstract: 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.
Cite: 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 OpenAlex
Dates:
Published print: May 1, 2009
Published online: Jun 9, 2009
Identifiers:
Web of science: WOS:000266829300001
Scopus: 2-s2.0-67049132873
Elibrary: 13604322
OpenAlex: W2008985315
Citing:
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Web of science 10
Scopus 7
Elibrary 7
OpenAlex 6
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