Biomimetic Total Synthesis and Investigation of the Non-Enzymatic Chemistry of Oxazinin A

Autor:	Victor Aniebok, Rahul D. Shingare, Hsiau Wei‐Lee, Timothy C. Johnstone, John B. MacMillan
Rok vydání:	2022
Předmět:	Biological Products Biomimetics Fungi General Medicine General Chemistry Heterocyclic Compounds 4 or More Rings Catalysis
Zdroj:	Angewandte Chemie (International ed. in English). 61(38)
ISSN:	1521-3773
Popis:	We report the first total synthesis of an antimycobacterial natural product oxazinin A that takes advantage of a multi-component cascade reaction of anthranilic acid and a precursor polyketide containing an aldehyde. The route utilized for the synthesis of the pseudodimeric oxazinin A validates a previously proposed biosynthetic mechanism, invoking a non-enzymatic pathway to the complex molecule. We found a 76 : 10 : 9 : 5 ratio of oxazinin diastereomers from the synthetic cascade, which is an identical match to that found in the fermentation media from the fungus Eurotiomycetes 110162. Further investigation of the non-enzymatic formation of oxazinin A using
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::2ed7d70668c0177aa3115e11b2bc6b26 https://pubmed.ncbi.nlm.nih.gov/35881566 Zobrazit plný text záznamu Plný text