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Issue 6, 2012
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Concise total synthesis of (+)-gliocladins B and C

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The first total synthesis of (+)-gliocladin B is described. Our concise and enantioselective synthesis takes advantage of a new regioselective Friedel–Crafts-based strategy to provide an efficient multigram-scale access to the C3-(3′-indolyl)hexahydropyrroloindole substructure, a molecular foundation present in a significant subset of epipolythiodiketopiperazine natural alkaloids. Our first-generation solution to (+)-gliocladin B involved the stereoselective formation of (+)-12-deoxybionectin A, a plausible biosynthetic precursor. Our synthesis clarified the C15 stereochemistry of (+)-gliocladin B and allowed its full structure confirmation. Further studies of a versatile dihydroxylated diketopiperazine provided a concise and efficient synthesis of (+)-gliocladin B as well as access to (+)-gliocladin C.

Graphical abstract: Concise total synthesis of (+)-gliocladins B and C

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The article was received on 05 Mar 2012, accepted on 30 Mar 2012 and first published on 30 Mar 2012

Article type: Edge Article
DOI: 10.1039/C2SC20270K
Citation: Chem. Sci., 2012,3, 1798-1803
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    Concise total synthesis of (+)-gliocladins B and C

    N. Boyer and M. Movassaghi, Chem. Sci., 2012, 3, 1798
    DOI: 10.1039/C2SC20270K

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