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      A Palladium-Catalyzed Carbo-oxygenation: The Bielschowskysin Case

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          Abstract

          An asymmetric synthesis of an advanced tetracyclic intermediate toward the synthesis of bielschowskysin ( 1) is described. A biomimetic [2 + 2]-photocyclization was used to establish the cyclobutane core of bielschowskysin. Macrocyclization under Heck conditions led to an unprecedented carbo-oxygenation of a 1,1-disubstituted double bond.

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          Most cited references8

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          Palladium-catalyzed carbohalogenation: bromide to iodide exchange and domino processes.

          Aryl bromides have been used to prepare a variety of nitrogen- and oxygen-containing heterocycles featuring new carbon-carbon and carbon-iodine bonds. This palladium-catalyzed carbohalogenation requires potassium iodide for the reaction to proceed in high yields. Additionally, the first examples of domino carbohalogenation reactions have been demonstrated using both aryl iodide and aryl bromide starting materials. Complex products with multiple rings and stereogenic centers are generated in excellent yields with moderate to excellent diastereoselectivities.
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            Pure Appl. Chem.

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              J. Am. Chem. Soc.

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                Author and article information

                Journal
                Org Lett
                Org. Lett
                ol
                orlef7
                Organic Letters
                American Chemical Society
                1523-7060
                1523-7052
                31 May 2013
                21 June 2013
                : 15
                : 12
                : 3098-3101
                Affiliations
                [1]University of Vienna , Department of Organic Chemistry, Währinger Str. 38, 1090 Vienna, Austria
                Author notes
                Article
                10.1021/ol401285d
                3691719
                23724910
                c076e73d-32ef-43ec-80d9-21c980aa20a1
                Copyright © 2013 American Chemical Society
                History
                : 10 May 2013
                Categories
                Letter
                Custom metadata
                ol401285d
                ol-2013-01285d

                Organic & Biomolecular chemistry
                Organic & Biomolecular chemistry

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