Redox Condensations of o-Nitrobenzaldehydes with Amines under Mild Conditions: Total Synthesis of the Vasicinone Family.

The Journal of Organic Chemistry
Oleg I AfanasyevDenis Chusov

Abstract

A total synthesis of the vasicinone family of natural products from bulk chemicals was developed. Reductive condensation of o-nitrobenzaldehydes with amines utilizing iron pentacarbonyl as a reducing agent followed by subsequent oxidation leads to a great variety of polycyclic nitrogen-containing heterocycles under mild conditions. Enantiomerically pure vasicinone, rutaecarpine, isaindigotone, and luotonin were synthesized from readily available starting materials like hydroxyproline, nitrobenzaldehyde, pyrrolidine, and piperidine in two to four operational steps without chromatography. The antifungal activity of all products was tested.

References

Dec 18, 2007·Journal of the American Chemical Society·Chen ZhangDaniel Seidel
Apr 2, 2008·Chemical & Pharmaceutical Bulletin·Katherine Chae JahngYurngdong Jahng
Sep 17, 2011·Current Medicinal Chemistry·P C SharmaH Rajak
Feb 16, 2012·Organic & Biomolecular Chemistry·Jie Fang, Jianguang Zhou
Dec 26, 2012·Journal of the American Chemical Society·Quyen NguyenTom G Driver
May 13, 2014·Chemical Communications : Chem Comm·Dan ZhaoJian-Xin Li
Dec 1, 2017·Organic & Biomolecular Chemistry·Oleg I AfanasyevDenis Chusov

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