Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2012, Issue 27, Pages 5151-5161Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201200712
Keywords
Total synthesis; Natural products; Cycloaddition; Biomimetic synthesis; Domino reactions; Cascade reactions
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The variecolortides are a family of unusual natural products that combine motifs from a variety of biosynthetic streams. Herein, we present the gradual evolution of a convergent synthetic strategy that ultimately culminated in a reaction cascade featuring a hydrogen shift and a cycloaddition followed by a spontaneous air oxidation. Attempts to link an anthrone building block with an exo-methylene diketopiperazine using radical chemistry were ultimately unsuccessful, but led to interesting observations that shaped our successful strategy. The total synthesis of variecolortide C is presented for the first time.
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