Synthesis of Enantiopure 2-C-Glycosyl-3-nitrochromenes

abstract

A novel methodology has been developed to obtain enantiopure 2-C-glycosyl-3-nitrochromenes. First, (Z)-1-bromo-1-nitroalkenes were prepared from the corresponding sugar aldehydes through a sodium iodide-catalyzed Henry reaction with bromonitromethane followed by elimination of the resulting 1-bromo-1-nitroalkan-2-ols. In the next step, reaction of the sugar-derived (Z)-1-bromo-1-nitroalkenes with o-hydroxybenzaldehydes afforded enantiopure (2S,3S,4S)-3-bromo-3,4-dihydro-4-hydroxy-3-nitro-2H-1-benzopyrans, which, upon SmI2-promoted beta-elimination, yielded chiral enantiopure 2-C-glycosyl-3-nitrochromenes.

keywords

POTASSIUM CHANNEL ACTIVATORS; SAMARIUM DIIODIDE; MILD CONDITIONS; STEREOCONTROLLED SYNTHESIS; ANTIHYPERTENSIVE ACTIVITY; CONVENIENT SYNTHESIS; 3-NITRO-2H-CHROMENES; DERIVATIVES; DEHYDRATION; CYCLIZATION

subject category

Chemistry

authors

Soengas, RG; Rodriguez-Solla, H; Silva, AMS; Llavona, R; Paz, FAA

our authors

acknowledgements

We thank the University of Aveiro, the Portuguese

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