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

Keywords

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

Publication Title

Tetrahedron

ISSN

0040-4020

Volume

58

Issue/No.

34

First Page

6843

Last Page

6849

Peer Reviewed

1

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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