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Oxidative coupling as a biomimetic approach to the synthesis of scytonemin.

ABSTRACT: 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.

SUBMITTER: Ekebergh A

PROVIDER: S-EPMC3164230 | biostudies-literature | 2011 Aug

REPOSITORIES: biostudies-literature

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Oxidative coupling as a biomimetic approach to the synthesis of scytonemin.

Ekebergh Andreas A Karlsson Isabella I Mete Rudi R Pan Ye Y Börje Anna A Mårtensson Jerker J

Organic letters 20110725 16

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 struct ...[more]

PMID: 21786790

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