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      Synthesis of Lasofoxifene, Nafoxidine and Their Positional Isomers via the Novel Three-Component Coupling Reaction

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          Abstract

          A Lewis acid-mediated three-component coupling reaction was successfully applied for the synthesis of lasofoxifene ( 1), nafoxidine ( 2), and their positional isomers, inv-lasofoxifene ( 3) and inv-nafoxidine ( 4). In the presence of HfCl 4, the desired one-pot coupling reaction among 4-pivaloyloxybenzaldehyde ( 5), cinnamyltrimethylsilane ( 6), and anisole proceeded to afford the corresponding 3,4,4-triaryl-1-butene 7 in high yield. The iodocarbocyclization of the coupling product and the successive elimination of hydrogen iodide forming the olefin part, followed by the migration of the double-bond afforded the common synthetic intermediate of lasofoxifene ( 1) and nafoxidine ( 2) via a very concise procedure. Additionally, the syntheses of their positional isomers inv-lasofoxifene ( 3) and inv-nafoxidine ( 4) were also achieved through very convenient protocols.

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          Most cited references 37

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          Multi-component cycloaddition approaches in the catalytic asymmetric synthesis of alkaloid targets

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            Recent progress in the chemistry of multicomponent reactions

             Ivar Ugi (2001)
            The chemistry of multicomponent reactions (MCRs) and isocyanides belongs to three periods: In the century 1859­1958, isocyanide chemistry was moderately active and was separate from the classical name reactions of the MCRs. In the next period, isocyanides became well available, and MCRs of isocyanides became the most variable way of forming chemical compounds. The year 1993 began a new era of the formation and investigation of the products and the libraries of the Ugi reaction (U-4CR) and higher MCRs of the isocyanides. This chemistry is primarily accomplished in the industrial search and preparation of new pharmaceutical and plant-protecting products.
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              I(py)2BF4, a New Reagent in Organic Synthesis: General Method for the 1,2-Iodofunctionalization of Olefins

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                Author and article information

                Journal
                Molecules
                Molecules
                molecules
                Molecules
                MDPI
                1420-3049
                28 September 2010
                October 2010
                : 15
                : 10
                : 6773-6794
                Affiliations
                Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan
                Author notes
                [* ]Author to whom correspondence should be addressed; E-Mail: shiina@ 123456rs.kagu.tus.ac.jp ; Fax: +81-3-3260-5609.
                Article
                molecules-15-06773
                10.3390/molecules15106773
                6259163
                © 2010 by the authors;

                licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license ( http://creativecommons.org/licenses/by/3.0/).

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