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Current Organic Chemistry

Editor-in-Chief

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

Intramolecular Haloetherification and Transannular Hydroxycyclization of Alkenes. A Synthetic Methodology to Obtain Polycyclic Ethers and Amines

Author(s): Angel M. Montana, Consuelo Batalla and Juan A. Barcia

Volume 13, Issue 9, 2009

Page: [919 - 938] Pages: 20

DOI: 10.2174/138527209788452135

Price: $65

Abstract

Intramolecular haloetherification and transannular hydroxycyclization of alkenes is a synthetic methodology to obtain polycyclic ethers and amines in a regio- and stereoselective manner. The stereoelectronic effects controlling this selectivity are discussed. Also, the methodology based on [4+3]-cycloaddition followed by intramolecular haloetherification or transannular hydroxycyclization is described as a very useful tool to prepare the dioxa- and oxazatricyclic cores of several bioactive natural products, whose molecular scaffold is quite difficult to reach by other synthetic approaches.

Keywords: Intramolecular haloetherification, transannular hydroxycyclization, alkenes, synthetic methodology, Polycyclic Ethers, natural products


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