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Open Access Direct Synthesis of Stereodefined and Functionalized Dienes as Valuable Building Blocks

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We have reported a direct and stereoselective synthesis of functionalized dienoic carboxylates from the simple bicyclic lactone 1. The use of oxygen- or nitrogen-based nucleophiles in a domino allylic alkylation/4π-electrocyclic ring opening affords reliable access to dienes with interesting functionalities. Alternatively, halide substitution offers synthesis of other classes of functionalized dienoic acids. Herein, we demonstrate the utility of such dienoic products as key building blocks in various transformations as well as natural product synthesis.

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Keywords: ALLYLIC ALKYLATION; AZIDE; DIENE; INTHOMYCIN C; RING OPENING

Document Type: Research Article

Affiliations: 1: University of Vienna Institute of Organic Chemistry Währinger Straße 38 A-1090 Vienna, Austria. [email protected] 2: University of Vienna Institute of Organic Chemistry Währinger Straße 38 A-1090 Vienna, Austria

Publication date: April 1, 2014

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  • International Journal for Chemistry and Official Membership Journal of the Swiss Chemical Society (SCS) and its Divisions

    CHIMIA, a scientific journal for chemistry in the broadest sense, is published 10 times a year and covers the interests of a wide and diverse readership. Contributions from all fields of chemistry and related areas are considered for publication in the form of Review Articles and Notes. A characteristic feature of CHIMIA are the thematic issues, each devoted to an area of great current significance.

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