Oxidative Coupling as a Biomimetic Approach to the Synthesis of Scytonemin
Journal article, 2011
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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aryl
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sunscreen scytonemin
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pigment
biosynthesis
cyanobacteria
derivatives
scope
Author
Andreas Ekebergh
Chalmers, Chemical and Biological Engineering, Organic Chemistry
Isabella Karlsson
University of Gothenburg
R. Mete
University of Gothenburg
Y. Pan
Chalmers, Chemical and Biological Engineering
Anna Börje
University of Gothenburg
Jerker Mårtensson
Chalmers, Chemical and Biological Engineering, Organic Chemistry
Organic Letters
1523-7060 (ISSN) 1523-7052 (eISSN)
Vol. 13 16 4458-4461Subject Categories
Chemical Sciences
DOI
10.1021/ol201812n