"Stereoselective Synthesis of Some Novel Heterocyclic Estrone Derivativ" by Eva Frank, Janos Wolfling et al.
 

Chemistry and Physics Faculty Articles

Title

Stereoselective Synthesis of Some Novel Heterocyclic Estrone Derivatives by Intramolecular 1,3-Dipolar Cycloaddition

Document Type

Article

Publication Date

8-2002

Publication Title

Tetrahedron

Keywords

Nitrones, Azomethine imines, 1, 3-dipolar cycloaddition, Lewis acid, Stereoselective synthesis

ISSN

0040-4020

Volume

58

Issue/No.

34

First Page

6843

Last Page

6849

Abstract

16,17-seco-3-Methoxyestra-1,3,5(10),16-tetraen-17-al undergoes intramolecular nitrone 1,3-dipolar cycloaddition with both hydroxylamine and N-methylhydroxylamine to produce a single isoxazolidine isomer in each case. The ring-closures of the hydrazones and the aldazine derived from the secoaldehyde lead to fused N-containing heterocycles via Lewis acid-induced cyclization of the intermediate azomethine imines.

DOI

10.1016/S0040-4020(02)00741-X

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