Multi-step reaction with 12 steps
1.1: sodium bis(2-methoxyethoxy)aluminium dihydride / dichloromethane; toluene / 22 h / 0 - 20 °C / Inert atmosphere
1.2: 1 h / 20 °C
2.1: pyridine / dichloromethane / 17 h / 0 - 20 °C / Inert atmosphere
3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 2 h / 20 °C
4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2 h / 20 °C / Inert atmosphere
5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / tetrahydrofuran / 168 h / 20 °C
6.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1.5 h / -72 °C / Inert atmosphere
7.1: titanium(IV) isopropylate; diethyl (2R,3R)-tartrate / dichloromethane / 0.75 h / -30 °C / Molecular sieve; Inert atmosphere
7.2: 15 h / -30 °C / Molecular sieve; Inert atmosphere
8.1: pyridine; tributylphosphine / 6.5 h / 20 - 50 °C / Inert atmosphere
9.1: dichloromethane; hexane / 19 h / -50 °C / Inert atmosphere
10.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 50 h / 20 °C / Inert atmosphere
11.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.75 h / 0 °C
12.1: lithium hexamethyldisilazane / tetrahydrofuran / 6 h / 0 - 20 °C / Inert atmosphere
With
pyridine; titanium(IV) isopropylate; diethyl (2R,3R)-tartrate; tributylphosphine; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; hexane; dichloromethane; water; dimethyl sulfoxide; toluene;
5.1: |Wittig Olefination / 7.1: |Sharpless Asymmetric Epoxidation / 7.2: |Sharpless Asymmetric Epoxidation;
DOI:10.1021/ol5006856