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FORMAL TOTAL SYNTHESES OF CROCACIN A-D

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Besev,  M.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Brehm,  C.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Fürstner,  A.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Besev, M., Brehm, C., & Fürstner, A. (2005). FORMAL TOTAL SYNTHESES OF CROCACIN A-D. Collection of Czechoslovak Chemical Communications, 70(10), 1696-1708. doi:10.1135/cccc20051696.


Cite as: https://hdl.handle.net/11858/00-001M-0000-000F-9523-B
Abstract
A concise route to the common polyketide fragment 5 of crocacin A-D (1-4) is presented which has previously been converted into all members of this fungicidal and cytotoxic family of dipeptidic natural products by various means. Our synthesis features a syn-selective titanium aldol reaction controlled by a valinol-derived auxiliary, a zinc-mediated, palladium-catalyzed anti-selective addition of propargyl mesylate 10 to the chiral aldehyde 9, as well as a comparison of palladium-catalyzed Stille and Suzuki cross-coupling reactions for the formation of the diene moiety of the target.