Multi-step reaction with 30 steps
1: 62 percent / <(R,R)-bis2O-)>-C(CH3)2>*CuOTf / CHCl3 / Ambient temperature
2: 1.) MeAl / 1.) toluene, from 0 deg C to RT, 30 min, 2.) toluene, RT, 30 min
3: 92 percent / N-methylmorpholine-N-oxide, tetra-n-propylammonium perruthenate, 4 Angstroem sieves / CH2Cl2; acetonitrile / 0.5 h / Ambient temperature
4: 1.) potassium hexamethyldisilazide / 1.) toluene, THF, from 0 deg C to RT, 30 min, 2.) toluene, THF, from -78 deg C to 0 deg C, 1 h
5: 1.) t-BuLi / 1.) ether, -78 deg C, 2.) ether
6: Et3N / -25 °C
7: 24 h / 110 °C
8: aq. HCl
9: 90 percent / tetrahydrofuran / 0 °C
10: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 23 °C
11: 1.) Red-Al, 2.) N-iodosuccinimide / 1.) Et2O, 23 deg C, 2.) Et2O, from -78 deg C to 23 deg C
12: 97 percent / imidazole / dimethylformamide
13: Pd(OAc)2, Ph3P, Ag2CO3 / tetrahydrofuran / Heating
14: tetrabutylammonium fluoride / tetrahydrofuran / 23 °C
15: 95 percent / N-methylmorpholin-N-oxide, tetra-n-propylammonium perruthenate
16: 1.) LiBr, Ni(acac)2 / 1.) Et2O, 0 deg C, 10 min, 2.) Et2O, RT, 17 h
17: 2-methoxy-1,3-dioxolane, Amberlyst-15 acidic resin / acetonitrile / 12 h / Ambient temperature
18: m-chloroperbenzoic acid, NaHCO3 / CH2Cl2 / 3 h / 0 - 20 °C
19: LiAlH4 / diethyl ether; tetrahydrofuran / 14 h / Ambient temperature
20: 20 percent aq. HCl / tetrahydrofuran / 12 h / 50 °C
21: N,N-diisopropylethylamine / CH2Cl2 / 7 h / Ambient temperature
22: 2.) Et3N / 1.) toluene, THF, 0 deg C, 10 h, 2.) THF, from 0 deg C to RT
23: 1M aq. HCl / tetrahydrofuran / 0.25 h / Ambient temperature
24: LiAlH4 / tetrahydrofuran / 0.5 h / -78 °C
25: pyridine, DMAP / CH2Cl2 / 2 h / 0 °C
26: 1.) LDA / 1.) hexane, THF, 0 deg C, 15 min, 2.) hexane, THF, 0 deg C, 2 h
27: K2CO3, KOH / methanol / 24 h / 140 °C
28: diethyl ether / 0.5 h / 0 °C
29: DMAP, pyridine / 5 h / 100 °C
30: aq. HCl / methanol / 0.75 h / 70 °C
With
2-methoxy-1,3-dioxolane; pyridine; 1H-imidazole; hydrogenchloride; dmap; palladium diacetate; bis(acetylacetonate)nickel(II); potassium hydroxide; N-iodo-succinimide; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; <(R,R)-bis-C(CH3)2>*CuOTf; 4 A molecular sieve; Amberlyst-15 acidic resin; tetrabutyl ammonium fluoride; tert.-butyl lithium; potassium hexamethylsilazane; sodium hydrogencarbonate; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; silver carbonate; lithium bromide; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja990404v