Synthesis of Laurencione, a Labile Dihydro-3(2H)-furanone Derivative from the Red Alga Laurencia spectabilis

Norbert De Kimpe, Angelina Georgieva, Marc Boeykens, Laszlo Lazar

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Abstract

The first total synthesis of laurencione, a naturally occurring dihydro-3(2H)-furanone derivative isolated from the red alga Laurencia spectabilis, is described. The synthesis is comprised (1) of conversion of γ-butyrolactone into α,α-dimethoxy-γ-butyrolactone, (2) addition of methyllithium across the lactone carbonyl, and (3) acid hydrolysis of the acetal moiety. An alternative synthesis consists of the acid-catalyzed conversion of 3,3-dimethoxy-2-hydroxy-2-methyltetrahydrofuran into laurencione methyl ether and subsequent acid-catalyzed hydrolysis. In addition, a convenient synthesis of the coffee and caramel flavor component 2-methyl-3(2H)-furanone has been developed by acid-catalyzed rearrangement of 2-methoxy-2-methyltetrahydrofuran-3-one.

Original languageEnglish
Pages (from-to)5262-5265
Number of pages4
JournalJournal of Organic Chemistry
Volume60
Issue number16
DOIs
Publication statusPublished - Aug 1 1995

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ASJC Scopus subject areas

  • Organic Chemistry

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