sodium methylate in methanol 0.5 h; Ambient temperature;

hydrogen in toluene T=20°C; Orito reaction; P=750.075 Torr; optical yield given as percent eeenantioselective reaction;

hydrogen in toluene T=20°C; Orito reaction; P=750.075 Torr; optical yield given as percent eeenantioselective reaction;

hydrogen in toluene T=20°C; Orito reaction; P=750.075 Torr; optical yield given as percent eeenantioselective reaction;

1: 1) butyllithium / 1) THF-hexane, -78 deg C, 2 h, 2) THF-hexane, room temp., overnight 2: pyridine / toluene; CH2Cl2 / Ambient temperature 3: 95 percent / HBF4 / tetrahydrofuran; H2O / 2 h / Ambient temperature 4: 51 percent / CsF / tetrahydrofuran / 48 h 5: 87 percent / trimethylsilyl chloride, tetrabutylammonium bromide / acetonitrile / 15 h / 40 °C 6: 56 percent / phosphopantetheine adenylyltransferase, dephosphocoenzyme A kinase, MgCl2, pyrophosphatase, pyruvate kinase, phospho(enol) pyruvate / H2O; various solvent(s) / 168 h / Ambient temperature 7: Crotalus atrox venom nucleotide pyrophosphatase EC 3.6.1.9 / H2O / 4 h 8: potato acid phosphatase EC 3.1.3.2 / H2O / 21 h View Scheme

(S)-(-)-BTM; N-ethyl-N,N-diisopropylamine in tetrahydrofuran T=-78°C; 24 h; Molecular sieveInert atmosphere; Reagent/catalystConcentrationSolventTemperature;

(S)-(-)-BTM; N-ethyl-N,N-diisopropylamine in tetrahydrofuran; toluene T=-78°C; 24 h; Molecular sieveInert atmosphere;

(S)-(-)-BTM; N-ethyl-N,N-diisopropylamine in tetrahydrofuran; toluene T=-78°C; 24 h; Molecular sieveInert atmosphere;

yeast lipase; butan-1-ol in di-isopropyl ether T=30°C; 336 h; Title compound not separated from byproducts;

osmium(VIII) oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III) in tert-butyl alcohol T=0°C; Oxidation; asymmetric dihydroxylation; 16 h; Title compound not separated from byproducts;