TY  - JOUR
AB  - Indigoids represent natural product-based compounds applicable as organic semiconductors and photoresponsive materials. Yet modified indigo derivatives are difficult to access by chemical synthesis. Thus a biocatalytic approach applying several consecutive selective C-H functionalizations was developed that selectively provides access to various indigoids: Enzymatic halogenation of l-tryptophan followed by indole generation with tryptophanase yields 5-, 6- and 7-bromoindoles. Subsequent hydroxylation using a flavin monooxygenase furnishes dibromoindigo that is derivatized by acylation. This four-step one-pot cascade gives Boc-protected dibromoindigo in good isolated yields. The halogen substituent allows for late-stage diversification by cross-coupling directly performed in the crude mixture, thus enabling synthesis of 5,5'- and 6,6'-diarylindigo derivatives. This chemoenzymatic approach provides a modular platform towards novel indigoids with attractive spectral properties. © 2021 Wiley-VCH GmbH.
DA  - 2021
DO  - 10.1002/chem.202005191
LA  - eng
IS  - 17
M2  - 5404
PY  - 2021
SP  - 5404-5411
T2  - Chemistry - A European Journal
TI  - Novel Arylindigoids by Late-Stage Derivatization of Biocatalytically Synthesized Dibromoindigo.
UR  - https://nbn-resolving.org/urn:nbn:de:0070-pub-29511524
Y2  - 2024-11-22T09:39:02
ER  -