188446-11-9

Upstream product

• 1080-06-4 L-Tyr-OMe 
• 24424-99-5 di-tert-butyl dicarbonate 
• 100-52-7 benzaldehyde 

Downstream Products

• 188446-17-5 (9S,12S)-12-(Benzyl-tert-butoxycarbonyl-amino)-4-nitro-11-oxo-2-oxa-10-aza-tricyclo[12.2.2.1^3,7]nonadeca-1⁽¹⁷⁾,3,5,7⁽¹⁹⁾,14⁽¹⁸⁾,15-hexaene-9-carboxylic acid methyl ester 
• 188446-15-3 (S)-2-[(S)-2-(Benzyl-tert-butoxycarbonyl-amino)-3-(4-hydroxy-phenyl)-propionylamino]-3-(3-fluoro-4-nitro-phenyl)-propionic acid methyl ester 
• 137622-55-0 (S)-2-(Benzyl-tert-butoxycarbonyl-amino)-3-(4-hydroxy-phenyl)-propionic acid 

Relevant academic research and scientific papers

A Bioinspired Synthesis of Polyfunctional Indoles

Polyfunctional indoles bearing substituents at C5 and C6 are prevalent in natural products, pharmaceuticals, agrochemicals, and materials. Owing to the remoteness of the C5 and C6 positions, indoles of this family can be difficult to prepare, and often require multistep syntheses. Herein, we describe a concise process that converts simple derivatives of tyrosine into 5,6-difunctionalized indoles by direct oxidation of C?H, N?H, and O?H bonds. Our work draws inspiration from the biosynthetic polymerization of tyrosine to make melanin pigments, but makes an important departure to provide well-defined indole heterocycles.

Synthesis of (9R,12S)- and (9S,12S)-cycloisodityrosine and their N-methyl derivatives

Full details of the synthesis of (9R,12S)- and (9S,12S)-cycloisodityrosine and their N-methyl derivatives are detailed based on an intramolecular nucleophilic aromatic substitution reaction for formation of the key biaryl ether with 14-membered ring macrocyclization. Their comparison with prior samples and the documentation of a facile C9 epimerization within the natural 9S series are described.