A facile route to the pentacyclic lamellarin skeleton via Grob reaction between 3-nitro-2-(trifluoromethyl)-2H-chromenes and 1,3,3-trimethyl-3,4-dihydroisoquinolines / Korotaev Vladislav Yu.,Sosnovskikh Vyacheslav Ya.,Kutyashev Igor B.,Barkov Alexey Yu.,Shklyaev Yurii V. // TETRAHEDRON LETTERS. - 2008. - V. 49, l. 37. - P. 5376-5379.

ISSN/EISSN:

0040-4039 / нет данных

Type:

Article

Abstract:

The basic structural framework of lamellarin alkaloids, 8,9-dihydro-6H-chromeno{[}4',3':4,5]pyrrolo{[}2,1-a)-isoquinoline derivatives, has been obtained in good yields via Grob reaction between 3-nitro-2-(trifluoromethyl)-2H-chromenes and 1,3,3-trimethyl-3,4-dihydroisoquinolines in refluxing isobutanol. When the reaction was carried out in toluene at room temperature, only Michael adducts, as a mixture of two diastereomers, were isolated. (c) 2008 Elsevier Ltd. All rights reserved.

Author keywords:

lamellarin skeleton; Grob reaction; 3-nitro-2-(trifluoromethyl)-2H-chromenes; 1,3,3-trimethyl-3,4-dihydroisoquinolines 3+2 CYCLOADDITION REACTIONS; ASCIDIAN DIDEMNUM-OBSCURUM; SUBSTITUTED PTEROCARPANS; POLYFLUOROCARBONYL COMPOUNDS; STEREOSELECTIVE-SYNTHESIS; REGIOSELECTIVE SYNTHESIS; MICHAEL-ADDITION; N-NUCLEOPHILES; C-NUCLEOPHILES; S-NUCLEOPHILES

DOI:

10.1016/j.tetlet.2008.06.122

Web of Science ID:

ISI:000258936000007

Соавторы в МНС:

Другие поля

Поле	Значение
Month	SEP 8
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	3+2 CYCLOADDITION REACTIONS; ASCIDIAN DIDEMNUM-OBSCURUM; SUBSTITUTED PTEROCARPANS; POLYFLUOROCARBONYL COMPOUNDS; STEREOSELECTIVE-SYNTHESIS; REGIOSELECTIVE SYNTHESIS; MICHAEL-ADDITION; N-NUCLEOPHILES; C-NUCLEOPHILES; S-NUCLEOPHILES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	vyacheslav.sosnovskikh@usu.ru
ResearcherID-Numbers	Korotaev, Vladislav/L-2692-2016
ORCID-Numbers	Korotaev, Vladislav/0000-0002-7492-5116
Funding-Acknowledgement	Russian Foundation for Basic Research {[}06-03-04004]
Funding-Text	This work was financially supported by the Russian Foundation for Basic Research (Grant 06-03-04004).
Number-of-Cited-References	49
Usage-Count-Since-2013	3
Journal-ISO	Tetrahedron Lett.
Doc-Delivery-Number	344OA