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

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

Journal Name: Current Organic Chemistry

Volume 13 , Issue 9 , 2009


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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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Article Details

VOLUME: 13
ISSUE: 9
Year: 2009
Published on: 01 March, 2012
Page: [919 - 938]
Pages: 20
DOI: 10.2174/138527209788452135
Price: $65

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