Synthesis of A-Pentacyclic Triterpene α,β-Alkenenitriles / Pereslavtseva A.V., Tolmacheva I.A., Slepukhin P.A., El'Tsov O.S., Kucherov I.I., Eremin V.F., Grishko V.V. // Chemistry of Natural Compounds. - 2014. - V. 49, l. 6. - P. 1059-1066.

ISSN:

00093130

Type:

Article

Abstract:

A-seco-triterpenoids with a methylketone group were synthesized from epimeric 3-hydroxy-3-methyl-1-cyano-2,3-seco-triterpenoids of the lupane and 19β,28-epoxy-18αH-oleanane types, which were formed by a Grignard reaction. The resulting methylketones underwent under base-catalysis conditions an intramolecular cyclization to form A-pentacyclic β-substituted alkenenitriles. The synthesized compounds included 3-methyl-1-cyano-19β,28- epoxy-2,3-seco-2-nor-18αH-olean-3-one and methyl 3-methyl-1-cyano-2- norlup-1(3),20(29)-dien-28-oate, which inhibited in vitro reproduction of human immunodeficiency virus type 1. © 2014 Springer Science+Business Media New York.

Author keywords:

α,β- alkenenitriles; A-seco-triterpenoids; allobetulone; betulonic acid; Grignard reaction; HIV-1; intramolecular oxonitrile cyclization; methylketones

Index keywords:

нет данных

DOI:

10.1007/s10600-014-0822-2

Смотреть в Scopus:

https://www.scopus.com/inward/record.uri?eid=2-s2.0-84894162347&doi=10.1007%2fs10600-014-0822-2&partnerID=40&md5=305050e6d50fbacf14a76ca5ee77ab79

Соавторы в МНС:

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Link	https://www.scopus.com/inward/record.uri?eid=2-s2.0-84894162347&doi=10.1007%2fs10600-014-0822-2&partnerID=40&md5=305050e6d50fbacf14a76ca5ee77ab79
Affiliations	Institute of Technical Chemistry, Ural Branch, Russian Academy of Sciences, 614013 Perm, Russian Federation; Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, 620219 Ekaterinburg, Russian Federation; El'Tsin Ural Federal University, 620002 Ekaterinburg, Russian Federation; RSPC of Epidemiology and Microbiology, Ministry of Health of the Republic of Belarus, 220114 Minsk, Belarus
Author Keywords	α,β- alkenenitriles; A-seco-triterpenoids; allobetulone; betulonic acid; Grignard reaction; HIV-1; intramolecular oxonitrile cyclization; methylketones
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Correspondence Address	Grishko, V.V.; Institute of Technical Chemistry, Ural Branch, Russian Academy of Sciences, 614013 Perm, Russian Federation; email: grishvic@gmail.com
CODEN	CHNCA
Language of Original Document	English
Abbreviated Source Title	Chem. Nat. Compd.
Source	Scopus