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Total Synthesis of (+)-Crocacin D

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Instituto de Química, Universidade Estadual de Campinas, UNICAMP, C. P. 6154 Campinas, SP, Brazil, and Ecole Normale Supérieure, Département de Chimie, 24, rue Lhomond, F-75231 Paris Cedex 05, France
Cite this: J. Org. Chem. 2005, 70, 6, 2225–2234
Publication Date (Web):February 17, 2005
https://doi.org/10.1021/jo047732k
Copyright © 2005 American Chemical Society

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    Abstract

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    The total synthesis of (+)-crocacin D is described. The convergent asymmetric synthesis relies on the use of a Stille cross-coupling between an (E)-vinyl stannane with an (E)-vinyl iodide to establish the (E,E)-dienamide moiety followed by a mild and efficient copper-catalyzed coupling between (+)-crocacin C and a (Z)-vinyl iodide to establish the challenging (Z)-enamide function.

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     Dedicated to Prof. Timothy John Brocksom for his outstanding contributions to the field of synthetic organic chemistry in Brazil.

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     FAX:  +55-019-3788-3023.

     Universidade Estadual de Campinas.

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     Ecole Normale Supérieure.

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    Experimental procedures and product characterization for compounds 5, 7, and 24 and selected IR, HRMS, and 1H and 13C NMR spectra for new compounds. This material is available free of charge via the Internet at http://pubs.acs.org.

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