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Current Organic Chemistry

Editor-in-Chief

ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Review Article

Diels-Alder Approaches for the Synthesis of Bridged Bicyclic Systems: Synthetic Applications of (7-hetero)norbornadienes

Author(s): Elena Moreno-Clavijo, Ana T. Carmona, Inmaculada Robina and Antonio J. Moreno-Vargas

Volume 20, Issue 22, 2016

Page: [2393 - 2420] Pages: 28

DOI: 10.2174/1385272820666160215235737

Price: $65

Abstract

Molecules containing bridged bicyclic systems, such as the (7-hetero)bicyclo[2.2.1]heptane ring system, are interesting synthetic targets because these systems are present in many molecules with biologically relevant activity. Common precursors for these sytems are the (7-hetero)nobornadienes. This review covers the different approaches used in the last ten years for the synthesis of (7-hetero)norbornadienes through Diels-Alder (D-A) cycloaddition between cyclic dienes and alkynes. The review also shows the synthetic applications of these [2.2.1]bicyclic systems as intermediates in the preparation of other relevant molecules.

Keywords: Alkyne dienophile, 7-azanorbornadiene, N-Boc-pyrrole, cyclopentadiene, furan, norbornadiene, 7-oxanorbornadiene, Diels-Alder cycloaddition.

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