92925-26-3Relevant academic research and scientific papers
Direct catalytic asymmetric synthesis of highly functionalized tetronic acids/tetrahydro-isobenzofuran-1,5-diones via combination of cascade three-component reductive alkylations and Michael-aldol reactions
Ramachary, Dhevalapally B.,Kishor, Mamillapalli
supporting information; experimental part, p. 2859 - 2867 (2010/08/21)
A practical and sustainable chemical process for the synthesis of highly substituted tetrahydro-isobenzofuran-1,5-diones was achieved for the first time through asymmetric cascade Michael-aldol reaction of 4-hydroxy-3-alkyl-5H-furan- 2-ones with alkyl vinyl ketones in the presence of a catalytic amount of l-proline or 9-amino-9-deoxyepiquinine/TCA. In this article, we discovered for the first time the asymmetric synthesis of privileged bicyclic lactones through kinetic resolution and show the synthetic application to pharmaceuticals and natural products synthesis.
Copper and cobalt mediated regioselective alkylation of polyketide models: Methyl 3,5-dioxohexanoate and triacetic acid lactone
Cervello, Jordi,Marquet, Jorge,Moreno-Manas, Marcial
, p. 2035 - 2046 (2007/10/02)
Regioselective C-alkylations at the intercarbonyl positions C-4 and C-2 of the polyketide model methyl 3,5-dioxohexanoate, 1, have been acomplished through reactions of its cobalt(II), 4a, and copper(II), 4b, complexes respectively. Some examples of double alkylations at both positions are presented. Cyclizations of the regioselectively substituted diketoesters so prepared gave triacetic acid lactone derivatives regioselectively alkylated at C-5 and at C-3.
COPPER COMPLEX PROTECTION IN THE REGIOSELECTIVE ALKYLATION OF METHYL 3,5-DIOXOHEXANOATE. PREPARATION OF 3-ALKYL DERIVATIVES OF 4-HYDROXY-6-METHYL-2-PYRONE
Cervello, Jordi,Marquet, Jorge,Moreno-Manas, Marcial
, p. 3715 - 3716 (2007/10/02)
Protection of the diketone moiety of the polyketide model methyl 3,5-dioxohexanoate by copper(II) complex formation followed by alkylation of the free C-2 position results in overall regioselective alkylation of the diketoester to afford methyl 2-alkyl-3,5-dioxohexanoates, which under cyclization afford 3-alkyl derivatives of triacetic acid lactone.
