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.

derivatives

biosynthesis

pigment

scope

cyanobacteria

1993

aryl

sunscreen scytonemin

p825

v49

oteau pj

Författare

Andreas Ekebergh

Chalmers, Kemi- och bioteknik, Organisk kemi

I. Karlsson

Göteborgs universitet

R. Mete

Göteborgs universitet

Y. Pan

Chalmers University of Technology

Anna Börje

Göteborgs universitet

Jerker Mårtensson

Chalmers, Kemi- och bioteknik, Organisk kemi

Organic Letters

1523-7060 (ISSN) 1523-7052 (eISSN)

Vol. 13 16 4458-4461

Ämneskategorier

Kemi

DOI

10.1021/ol201812n