Reaction of C 3 and C 4 ketoses with alkenals and alkenones in water

• Published in: Tetrahedron letters Vol. 45; no. 48; pp. 8777 - 8780
• Main Authors: Saimoto, Hiroyuki, Onitsuka, Tomoyuki, Motobe, Hironobu, Okabe, Satoko, Takamori, Yoshimori, Morimoto, Minoru, Shigemasa, Yoshihiro
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 22-11-2004
• Subjects: Dihydroxyacetone; Erythrulose; One-pot reaction; Tetrahydrofurans; Water; Water; Dihydroxyacetone; Erythrulose; One-pot reaction; Tetrahydrofurans
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2004.10.004

Tetrahydrofuran derivatives were synthesized by the one-pot reaction of 1,3-dihydroxyacetone with α,β-unsaturated aldehydes and ketones in aqueous NaOH or KOH. This sequence is successfully applied to the reaction of
l-(
S)-erythrulose with 2-cyclopentenone to give tricyclic tetrahydrofuran derivatives in the absence of any protecting groups.
Treatment of 1,3-dihydroxyacetone and acrolein with aqueous KOH gave a tetrahydrofuran derivative, 1,4-dihydroxy-3,7-dioxabicyclo[3.3.0]octane, in 80% yield. Similarly, 6-alkyl substituted 1,4-dihydroxy-3,7-dioxabicyclo[3.3.0]octanes were obtained by reaction of 1,3-dihydroxyacetone with various α,β-unsaturated aldehydes. In the cases of long chain alkenals, the reaction was effectively accelerated in the presence of organic co-solvent. On the other hand, the corresponding tricyclic products were synthesized by reaction of 1,3-dihydroxyacetone with cyclic enones, such as 2-cyclopentenone and 2-cyclohexenone. This method was successfully applied to the reaction of a tetrulose in the absence of any protecting groups.