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. https://dx.doi.org/10.1055/s-1996-4335
In: Synthesis. Thieme: Stuttgart. ISSN 0039-7881; e-ISSN 1437-210X, meer
|  |
| Trefwoorden |
Laurencia spectabilis Postels & Ruprecht, 1840 [WoRMS]
Marien/Kust |
| Author keywords |
laurencione; marine natural product; alpha-haloimine; alpha-diones;tetrahydrofurans |
| Auteurs | | 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. |
|
