Oxidative Coupling as a Biomimetic Approach to the Synthesis of Scytonemin
Artikel i vetenskaplig tidskrift, 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.
oteau pj
p825
aryl
v49
sunscreen scytonemin
1993
pigment
biosynthesis
cyanobacteria
derivatives
scope
Författare
Andreas Ekebergh
Chalmers, Kemi- och bioteknik, Organisk kemi
Isabella Karlsson
Göteborgs universitet
R. Mete
Göteborgs universitet
Y. Pan
Chalmers, Kemi- och bioteknik
Anna Börje
Göteborgs universitet
Jerker Mårtensson
Chalmers, Kemi- och bioteknik, Organisk kemi
Organic Letters
1523-7060 (ISSN) 1523-7052 (eISSN)
Vol. 13 16 4458-4461Ämneskategorier
Kemi
DOI
10.1021/ol201812n