Oxidative Coupling as a Biomimetic Approach to the Synthesis of Scytonemin | Zendy

Andreas Ekebergh | Zendy; Isabella Karlsson | Zendy; Rudi Mete | Zendy; Pan Ye | Zendy; Anna Börje | Zendy; Jerker Mårtensson | Zendy

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Oxidative Coupling as a Biomimetic Approach to the Synthesis of Scytonemin

Author(s) -

Andreas Ekebergh,

Isabella Karlsson,

Rudi Mete,

Pan Ye,

Anna Börje,

Jerker Mårtensson

Publication year - 2011

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol201812n

Subject(s) - chemistry , tandem , stereochemistry , stereospecificity , oxidative phosphorylation , oxidative coupling of methane , acetic acid , combinatorial chemistry , organic chemistry , biochemistry , catalysis , materials science , composite material

The first total synthesis of the dimeric alkaloid pigment scytonemin is described. The key transformations in its synthesis from 3-indole acetic acid are a Heck carbocyclization and a Suzuki-Miyaura cross-coupling, orchestrated in a stereospecific tandem fashion, followed by a biosynthetically inspired oxidative dimerization. The tandem sequence generates a tetracyclic (E)-3-(arylidene)-3,4-dihydrocyclopenta[b]indol-2(1H)-one that is subsequently dimerized into the unique homodimeric core structure of scytonemin.

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