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 |
Call for Papers in Thematic Issues
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
Chemistry and Biology of Carbohydrates
Carbohydrates are one of the most abundant natural products and are considered to be extremely important biomolecules for their ever-increasing impact on chemistry and biology. Their role in several important biological processes, notably energy storage, transport, modulation of protein function, intercellular adhesion, malignant transformation, signal transduction, viral, and bacterial cell ...read more
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