Synthesis p. 303 - 306 (1995)
Update date:2022-09-26
Topics:
Cottier
Descotes
Eymard
Rapp
The photooxygenation of 5-hydroxymethyl-2-furfural (1a) or derivatives 1b-g yields 4-hydroxy-Δ2-butenolides 2 which are the percursors of butenolides 3 or α,β-unsaturated γ-oxo esters 5. The selective reduction of olides 2 or oxo esters 5 with zinc in acetic acid under sonication leads to γ-oxo acids 4 or γ-oxo esters 6. The photooxygenation of amino derivative 1d, followed by selective reduction of corresponding lactone 2d, gives 5-aminolevulinic acid hydrochloride (7) (ALA) after hydrolysis.
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(1997)Doi:10.1021/ja00399a062
(1981)Doi:10.1016/0957-4166(95)00210-G
(1995)Doi:10.1002/hlca.200490234
(2004)Doi:10.1021/jo00027a036
(1992)