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
Current Organic Chemistry
Title: Intramolecular Haloetherification and Transannular Hydroxycyclization of Alkenes. A Synthetic Methodology to Obtain Polycyclic Ethers and Amines
Volume: 13 Issue: 9
Author(s): Angel M. Montana, Consuelo Batalla and Juan A. Barcia
Affiliation:
Keywords: Intramolecular haloetherification, transannular hydroxycyclization, alkenes, synthetic methodology, Polycyclic Ethers, natural products
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.
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Montana M. Angel, Batalla Consuelo and Barcia A. Juan, Intramolecular Haloetherification and Transannular Hydroxycyclization of Alkenes. A Synthetic Methodology to Obtain Polycyclic Ethers and Amines, Current Organic Chemistry 2009; 13 (9) . https://dx.doi.org/10.2174/138527209788452135
DOI https://dx.doi.org/10.2174/138527209788452135 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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