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.
v49
cyanobacteria
p825
sunscreen scytonemin
pigment
1993
biosynthesis
aryl
scope
derivatives
oteau pj
Author
Andreas Ekebergh
Chalmers, Chemical and Biological Engineering, Organic Chemistry
I. Karlsson
Goteborgs Universitet
R. Mete
Goteborgs Universitet
Y. Pan
Chalmers University of Technology
Anna Börje
Goteborgs Universitet
Jerker Mårtensson
Chalmers, Chemical and Biological Engineering, Organic Chemistry
Organic Letters
1523-7060 (ISSN) 1523-7052 (eISSN)
Vol. 13 16 4458-4461Subject Categories (SSIF 2011)
Chemical Sciences
DOI
10.1021/ol201812n