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Oxidative Coupling as a Biomimetic Approach to the Synthesis of Scytonemin

Andreas Ekebergh (Institutionen för kemi- och bioteknik, Organisk kemi) ; I. Karlsson ; R. Mete ; Y. Pan ; A. Borje ; Jerker Mårtensson (Institutionen för kemi- och bioteknik, Organisk kemi)
Organic Letters (1523-7060). Vol. 13 (2011), 16, p. 4458-4461.
[Artikel, refereegranskad vetenskaplig]

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.

Nyckelord: sunscreen scytonemin, pigment, cyanobacteria, biosynthesis, derivatives, scope, aryl, oteau pj, 1993, v49, p825

Denna post skapades 2011-09-29. Senast ändrad 2017-10-03.
CPL Pubid: 146703


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Institutioner (Chalmers)

Institutionen för kemi- och bioteknik, Organisk kemi (2006-2014)



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The cyanobacterial pigments scytonemin and nostodione A - Synthesis, photophysicochemical behavior and biological studies