Journal
ORGANIC LETTERS
Volume 13, Issue 16, Pages 4458-4461Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol201812n
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Funding
- Swedish Research Council
- Centre for Skin Research at University of Gothenburg
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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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