Multi-step reaction with 21 steps
1.1: hydroquinidein 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III); osmium(VIII) oxide; methanesulfonamide; potassium carbonate / water; tert-butyl alcohol / 23 h / 0 °C
2.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C
3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1.17 h / 20 °C / pH 7
4.1: triethylamine; dmap / dichloromethane / 25 h / 0 - 20 °C
5.1: sodium iodide / acetone / 18 h / 50 °C
6.1: 9-methoxy-9-BBN; tert.-butyl lithium / tetrahydrofuran; hexane; diethyl ether; pentane / 4 h / -78 - 20 °C
6.2: 0.33 h / 20 °C
6.3: 13 h / 50 °C
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C
8.1: pyridinium p-toluenesulfonate / dichloromethane / 7.5 h / 0 - 20 °C
9.1: acetic acid / tetrahydrofuran; water / 16 h / 20 °C
10.1: pyridinium p-toluenesulfonate / dichloromethane / 2 h / 20 °C
11.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 - 20 °C
11.2: 12 h / 0 - 20 °C
12.1: diisobutylaluminium hydride / dichloromethane; hexane / 2.25 h / -78 °C
13.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 2 h / 0 °C
14.1: triethylamine; di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 1 h / 0 °C
14.2: 2.25 h / -78 - 0 °C
14.3: 1 h / 0 °C
15.1: pyridine; silver nitrate / N,N-dimethyl-formamide / 1 h / 20 °C
16.1: lithium borohydride / tetrahydrofuran; water / 16.7 h / 0 - 20 °C
17.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 0.67 h / 0 - 20 °C
18.1: boron trifluoride diethyl etherate / dichloromethane; diethyl ether / 0.28 h / -78 °C
19.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 0.67 h / 0 - 20 °C
20.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; borane-THF / tetrahydrofuran; toluene / 7.3 h / -40 °C
21.1: dmap; pyridine / tetrahydrofuran / 4 h / 0 - 20 °C
With
pyridine; 2,6-dimethylpyridine; dmap; osmium(VIII) oxide; lithium borohydride; borane-THF; methanesulfonamide; di-n-butylboryl trifluoromethanesulfonate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tert.-butyl lithium; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; silver nitrate; acetic acid; hydroquinidein 1,4-phthalazinediyl diether; triethylamine; 9-methoxy-9-BBN; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; potassium hexacyanoferrate(III); (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; mineral oil; tert-butyl alcohol; pentane;
1.1: |Sharpless Dihydroxylation / 14.1: |Evans Aldol Reaction / 14.2: |Evans Aldol Reaction / 18.1: |Mukaiyama Aldol Addition;
DOI:10.1021/ol4017518