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New formal syntheses of laurencione, a labile dihydrofuranone derivative from the red alga Laurencia spectabilis
De Kimpe, N.; Georgieva, A.; Boeykens, M.; Kozekov, I.; Aelterman, W. (1996). New formal syntheses of laurencione, a labile dihydrofuranone derivative from the red alga Laurencia spectabilis. Synthesis 1996(9): 1131-1134. hdl.handle.net/10.1055/s-1996-4335
In: Synthesis. Thieme: Stuttgart. ISSN 0039-7881, more
Peer reviewed article  

Available in Authors 

Keyword
    Marine
Author keywords
    laurencione; marine natural product; alpha-haloimine; alpha-diones;tetrahydrofurans

Authors  Top 
  • De Kimpe, N.
  • Georgieva, A.
  • Boeykens, M.
  • Kozekov, I.
  • Aelterman, W.

Abstract
    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.

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