Structure-reactivity relationship in 19-methyl-and 19-nor-5,10-secosteroids. Part 4. Intramolecular nitrone 1,3-dipolar cycloadditions

Autor:	Mihailo Lj. Mihailović, Aleksandar Z̆. Milovanović, Bernard Tinant, Jean-Paul Declercq, Lj. Lorenc, Vladimir D. Pavlović, M. Rajkovic
Rok vydání:	1996
Předmět:	chemistry.chemical_classification Ketone Hydrochloride Stereochemistry Organic Chemistry Biochemistry Cycloaddition Nitrone Secosteroids chemistry.chemical_compound chemistry Intramolecular force Drug Discovery Structural isomer Derivative (chemistry)
Zdroj:	Tetrahedron. 52:11995-12008
ISSN:	0040-4020
DOI:	10.1016/0040-4020(96)00694-1
Popis:	The (Z)-19-nor-5,10-secosteroidal ketone 11 reacts with hydroxylamine hydrochloride to give the (E)- and (Z)-oximes 12 and 13, while with N-methylhydroxylamine hydrochloride it undergoes transannular nitrone 1,3-dipolar cycloaddition to give isoxazolidines 14 and 15, and an estratriene derivative 16, originating from 14. The (E)-19-nor-5,10-seco-ketone 17 undergoes intramolecular nitrone 1,3-dipolar cycloaddition with both hydroxylamine hydrochloride and N-methylhydroxylamine hydrochloride to produce, with the former reagent, a single isoxazolidine 18, and with the latter, two regioisomers 22 and 23. The reaction and stereochemical courses of the above transformations are compared with those previously observed for the corresponding 19-methyl analogues. Copyright (C) 1996 Published by Elsevier Science Ltd.
Databáze:	OpenAIRE
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