Synthesis of the germination stimulant 3-methyl-2H-furo[2,3-c]pyran-2-one and analogous compounds from carbohydrates

Abstract

An efficacious synthetic route to the recently identified, potent germination stimulant 3-methyl-2H-furo[2,3-c]pyran-2-one and analogous compounds, using carbohydrate substrates, is described. D-Xylose and D-glucuronic acid γ-lactone were used in the preparation of the parent heterocycle and its 5-methoxycarbonyl analogue, respectively. These compounds were elaborated using various methods to furnish the natural product and a suite of its analogues. The germination stimulant was thus prepared on a multi-gram scale in nine steps from inexpensive, commercially available 1,2-O-isopropylidene-D-xylofuranose in an overall yield of 30 %, vastly improving upon the only method published to date. © W..