Total synthesis of inubosin B. Issue 52 (24th December 2020)

• Record Type: Journal Article
• Authors: Hamissa, Mohamed Farouk; Niederhafner, Petr; Šafařík, Martin; Telus, Marta; Kolářová, Lenka; Koutná, Leah; Šestáková, Hana; Souček, Radko; Šebestík, Jaroslav
• Is Part Of: Tetrahedron letters. Volume 61:Issue 52(2020)
• Publication Date: 2020-12-24
• Subjects: Neuroregeneration -- Neurodegeneration -- Acridine -- Alkaloid -- Total synthesis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2020.152641
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Total synthesis of Inubosin B. Over reduction reactions. Reverse phase removal of aluminum from oxine like chelators. Abstract: Inubosin B is the most active member of the acridine alkaloids isolated from Streptomyces sp. IFM 11440 culture. The inubosins initiate neuroregeneration via a neurogenine 2 pathway. In this work, we have described the total synthesis of inubosin B via two synthetic routes. The effects of various coupling, cyclization and reduction reactions are discussed including common pitfalls and side reactions. Reverse phase chromatography with TFA was crucial for the isolation of the product from aluminum ions present in the reduction media.