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Synthesis 1996; 1996(9): 1131-1134
DOI: 10.1055/s-1996-4335
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New Formal Syntheses of Laurencione, a Labile Dihydrofuranone Derivative from the Red Alga Laurencia spectabilis

Norbert De Kimpe* , Angelina Georgieva, Marc Boeykens, Ivan Kozekov, Wim Aelterman
  • *Department of Organic Chemistry, Faculty of Agricultural and Applied Biological Sciences, University of Gent, Coupure Links 653, B-9000 Gent, Belgium, Fax +32(9)2646243
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Publication Date:
31 December 2000 (online)

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A straightforward formal synthesis of the marine natural products laurencione was developed, utilizing elaboration of 5-acetoxy-3-chloropentan-2-one as the starting compound. The synthetic route consisted of (i) α-sulfenylation, (ii) α-chlorination of the resulting β-oxo sulfide, (iii) Hg2+-catalyzed methanolysis, (iv) methanolysis of the γ-acetoxy-α,α-dimethoxy ketone with subsequent cyclization and (v) acid hydrolysis of the acetal. Alternatively, laurencione was prepared from 1,1-dichloroacetone by a sequence of reactions involving (i) imination, (ii) regiospecific β-hydroxyethylation, (iii) hydrolysis, (iv) base-induced rearrangement of the resulting functionalized tetrahydrofuran and (v) final acid hydrolysis of laurencione methyl ether.

laurencione - marine natural product - α-haloimine - α-diones - tetrahydrofurans

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