The Development of a General Strategy for the Synthesis of Tyramine-Based Natural Products by Using Continuous Flow Techniques

• Published in: Chemistry : a European journal Vol. 16; no. 43; pp. 12797 - 12800
• Main Authors: Achanta, Srinivas, Liautard, Virginie, Paugh, Robert, Organ, Michael G.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 15.11.2010; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Subjects: Biological Products - chemical synthesis; Biological Products - chemistry; Chemistry; Chemistry, Multidisciplinary; Chemistry, Pharmaceutical - methods; Combinatorial Chemistry Techniques; flow chemistry; Heck reaction; microwave chemistry; Microwaves; Molecular Structure; Physical Sciences; Science & Technology; Temperature; tyramine; Tyramine - analogs & derivatives; Tyramine - chemical synthesis; Tyramine - chemistry; THIN-FILMS; GOLD; CAPILLARIES; microwave chemistry; Heck reaction; tyramine; INHIBITOR; ORGANIC-SYNTHESIS MACOS; flow chemistry; AMIDES
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201002102

A flowing future! A multistep, general flow chemistry protocol has been developed for the preparation of tyramine‐based natural products. The process integrates room‐temperature reactions with high‐temperature Heck coupling reactions, where the heat has been supplied by microwave irradiation. As a proof of concept for ‘scaling out’ to attain larger quantities of the desired products, the four primary tyramine‐based natural products were prepared on a gram scale using this synthetic protocol.