An unprecedented 5,6-dihydroxyindole macrocycle I featuring a rigid twisted backbone was obtained by biomimetic oxidative cross-coupling of the 2,2'-biindole II and triindole III. A putative reaction intermediate, 2-quinone IV, was detected and characterized by pulse radiolysis and DFT calcns. Discovery of I indirectly supports for the first time theor. predicted cyclic structural motifs as potential eumelanin building blocks.

Cyclic Structural Motifs in 5,6-Dihydroxyindole Polymerization Uncovered: Biomimetic Modular Buildup of a Unique Five-Membered Macrocycle / Arzillo, Marianna; Pezzella, Alessandro; Crescenzi, Orlando; Napolitano, Alessandra; E. J., Land; V., Barone; D'Ischia, Marco. - In: ORGANIC LETTERS. - ISSN 1523-7060. - STAMPA. - 12:14(2010), pp. 3250-3253. [10.1021/ol101188c]

Cyclic Structural Motifs in 5,6-Dihydroxyindole Polymerization Uncovered: Biomimetic Modular Buildup of a Unique Five-Membered Macrocycle

ARZILLO, MARIANNA;PEZZELLA, ALESSANDRO;CRESCENZI, ORLANDO;NAPOLITANO, ALESSANDRA;D'ISCHIA, MARCO
2010

Abstract

An unprecedented 5,6-dihydroxyindole macrocycle I featuring a rigid twisted backbone was obtained by biomimetic oxidative cross-coupling of the 2,2'-biindole II and triindole III. A putative reaction intermediate, 2-quinone IV, was detected and characterized by pulse radiolysis and DFT calcns. Discovery of I indirectly supports for the first time theor. predicted cyclic structural motifs as potential eumelanin building blocks.
2010
Cyclic Structural Motifs in 5,6-Dihydroxyindole Polymerization Uncovered: Biomimetic Modular Buildup of a Unique Five-Membered Macrocycle / Arzillo, Marianna; Pezzella, Alessandro; Crescenzi, Orlando; Napolitano, Alessandra; E. J., Land; V., Barone; D'Ischia, Marco. - In: ORGANIC LETTERS. - ISSN 1523-7060. - STAMPA. - 12:14(2010), pp. 3250-3253. [10.1021/ol101188c]
Cyclic Structural Motifs in 5,6-Dihydroxyindole Polymerization Uncovered: Biomimetic Modular Buildup of a Unique Five-Membered Macrocycle / Arzillo, Marianna; Pezzella, Alessandro; Crescenzi, Orlando; Napolitano, Alessandra; E. J., Land; V., Barone; D'Ischia, Marco. - In: ORGANIC LETTERS. - ISSN 1523-7060. - STAMPA. - 12:14(2010), pp. 3250-3253. [10.1021/ol101188c]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11588/370618
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