Reaction of C3 and C4 ketoses with alkenals and alkenones in water

Autor:	Yoshihiro Shigemasa, Minoru Morimoto, Tomoyuki Onitsuka, Hiroyuki Saimoto, Hironobu Motobe, Satoko Okabe, Yoshimori Takamori
Rok vydání:	2004
Předmět:	Aqueous solution Organic Chemistry Acrolein Dihydroxyacetone Erythrulose General Medicine Biochemistry chemistry.chemical_compound chemistry Yield (chemistry) Drug Discovery Organic chemistry Long chain Derivative (chemistry) Tetrahydrofuran Octane
Zdroj:	Tetrahedron Letters. 45:8777-8780
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2004.10.004
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::c14f674767d05caacc64fb5a02b4d89b https://doi.org/10.1016/j.tetlet.2004.10.004 Zobrazit plný text záznamu Full Text from ScienceDirect