Multi-step reaction with 20 steps
1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 2 h / 20 °C
2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2 h / 20 °C / Inert atmosphere
3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / tetrahydrofuran / 168 h / 20 °C
4.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1.5 h / -72 °C / Inert atmosphere
5.1: titanium(IV) isopropylate; diethyl (2R,3R)-tartrate / dichloromethane / 0.75 h / -30 °C / Molecular sieve; Inert atmosphere
5.2: 15 h / -30 °C / Molecular sieve; Inert atmosphere
6.1: pyridine; tributylphosphine / 6.5 h / 20 - 50 °C / Inert atmosphere
7.1: dichloromethane; hexane / 19 h / -50 °C / Inert atmosphere
8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 50 h / 20 °C / Inert atmosphere
9.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.75 h / 0 °C
10.1: lithium hexamethyldisilazane / tetrahydrofuran / 6 h / 0 - 20 °C / Inert atmosphere
11.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C
12.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 20 °C
13.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; borane-THF / toluene; tetrahydrofuran / 1.17 h / -40 °C / Inert atmosphere
14.1: titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate / dichloromethane / 18 h / -30 °C / Molecular sieve; Inert atmosphere
15.1: copper(l) iodide / diethyl ether / 23 h / -70 - 20 °C / Inert atmosphere
15.2: 4 h / 20 °C
16.1: aluminum (III) chloride / 1 h / 0 °C / Inert atmosphere
17.1: toluene-4-sulfonic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere
18.1: pyridinium p-toluenesulfonate / 0.33 h / 20 °C / Inert atmosphere
19.1: N,N,N,N,-tetramethylethylenediamine / diethyl ether / 2 h / 20 °C / Inert atmosphere
20.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.33 h / 20 °C / Inert atmosphere
With
pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; aluminum (III) chloride; copper(l) iodide; tetrapropylammonium perruthennate; borane-THF; diethyl (2R,3R)-tartrate; L-(+)-diisopropyl tartrate; N,N,N,N,-tetramethylethylenediamine; tributylphosphine; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; toluene;
3.1: |Wittig Olefination / 5.1: |Sharpless Asymmetric Epoxidation / 5.2: |Sharpless Asymmetric Epoxidation / 13.1: |Corey-Bakshi-Shibata Reduction / 14.1: |Sharpless Asymmetric Epoxidation;
DOI:10.1021/ol5006856