Synthesis of the Germination Stimulant 3‐Methyl‐2H‐furo[2,3‐c]pyran‐2‐one and Analogous Compounds from Carbohydrates

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.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)