Journal of Organic Chemistry p. 5262 - 5265 (1995)
Update date:2022-08-10
Topics:
De Kimpe
Georgieva
Boeykens
Lazar
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.
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