lithium aluminium tetrahydride in tetrahydrofuran; diethyl ether 2 h; Ambient temperature; Yield given;

1: 82 percent / ethanol; CHCl3; diethyl ether / 1 h / 0 °C 2: 81 percent / NaOMe / methanol; CHCl3 / 96 h / Ambient temperature 3: LiAlH4 / tetrahydrofuran; diethyl ether / 27 h / Heating 4: pyridine / 1.5 h / Ambient temperature 5: LiAlH4 / tetrahydrofuran; diethyl ether / 2 h / Ambient temperature View Scheme

1: 81 percent / NaOMe / methanol; CHCl3 / 96 h / Ambient temperature 2: LiAlH4 / tetrahydrofuran; diethyl ether / 27 h / Heating 3: pyridine / 1.5 h / Ambient temperature 4: LiAlH4 / tetrahydrofuran; diethyl ether / 2 h / Ambient temperature View Scheme

1: pyridine / 1.5 h / Ambient temperature 2: LiAlH4 / tetrahydrofuran; diethyl ether / 2 h / Ambient temperature View Scheme

1: LiAlH4 / tetrahydrofuran; diethyl ether / 27 h / Heating 2: pyridine / 1.5 h / Ambient temperature 3: LiAlH4 / tetrahydrofuran; diethyl ether / 2 h / Ambient temperature View Scheme

2,3-dihydroxybutanedioic acid in water 144 h; biosynthesis in Cocculus laurifolius DC (Menispermaceae);

2,3-dihydroxybutanedioic acid in water 144 h; biosynthesis in Cocculus laurifolius DC (Menispermaceae);