Cyclic Structural Motifs in 5,6-Dihydroxyindole Polymerization Uncovered: Biomimetic Modular Buildup of a Unique Five-Membered Macrocycle
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- 作者：Marianna Arzillo ; Alessandro Pezzella ; Orlando Crescenzi ; Alessandra Napolitano ; Edward J. Land ; Vincenzo Barone ; Marco d’ ; Ischia
- 刊名：Organic Letters
- 出版年：2010
- 出版时间：July 16, 2010
- 年：2010
- 卷：12
- 期：14
- 页码：3250-3253
- 全文大小：202K
- 年卷期：v.12,no.14(July 16, 2010)
- ISSN：1523-7052
文摘
An unprecedented 5,6-dihydroxyindole macrocycle (4) featuring a rigid twisted backbone was obtained by biomimetic oxidative cross-coupling of the 2,2′-biindole 2 and triindole 3. A putative reaction intermediate, 2-quinone, was detected and characterized by pulse radiolysis and DFT calculations. Discovery of 4 indirectly supports for the first time theoretically predicted cyclic structural motifs as potential eumelanin building blocks.