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Molecules 2015, 20(1), 1475-1494; doi:10.3390/molecules20011475

Seven-Membered Rings through Metal-Free Rearrangement Mediated by Hypervalent Iodine

1
Departamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, CP 26077, São Paulo-SP CEP 05513-970, Brazil
2
Division of Pharmacology and Toxicology, Multidisciplinary Center for Chemical, Biological and Agricultural, State University of Campinas, 6171, Campinas-SP CEP 13081-970, Brazil
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 2 December 2014 / Accepted: 8 January 2015 / Published: 15 January 2015
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [1111 KB, uploaded 15 January 2015]   |  

Abstract

A versatile and metal-free approach for the synthesis of carbocycles and of heterocycles bearing seven- and eight-membered rings is described. The strategy is based on ring expansion of 1-vinylcycloalkanols (or the corresponding silyl or methyl ether) mediated by the hypervalent iodine reagent HTIB (PhI(OH)OTs). Reaction conditions can be easily adjusted to give ring expansion products bearing different functional groups. A route to medium-ring lactones was also developed. View Full-Text
Keywords: hypervalent iodine; ring expansion; rearrangement; seven-membered ring; antiproliferative activity hypervalent iodine; ring expansion; rearrangement; seven-membered ring; antiproliferative activity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Silva, S.B.L.; Torre, A.D.; de Carvalho, J.E.; Ruiz, A.L.T.G.; Silva, L.F., Jr. Seven-Membered Rings through Metal-Free Rearrangement Mediated by Hypervalent Iodine. Molecules 2015, 20, 1475-1494.

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