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

E.D. Goddard-Borger, Emilio Ghisalberti, Robert Stick

Research output: Contribution to journalArticle

47 Citations (Scopus)

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 gamma-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. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).
Original languageEnglish
Pages (from-to)3925-3934
JournalEuropean Journal of Organic Chemistry
Volume2007
Issue number23
DOIs
Publication statusPublished - 2007

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