Multi-step reaction with 23 steps
1: O3
2: KMnO4, KH2PO4
4: 93 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C
5: 100 percent / p-TsOH
6: 92 percent / PhSK / dimethylformamide / 3 h / 86 °C
7: acid
8: 92 percent / EtN(i-Pr)2, (Bu)4NI / CH2Cl2 / 32 h / Heating
9: 1.) LDA, 2.) mCPBA / 1.) THF, -78 deg C, 2.) hexane, 25 deg C, 5 h
10: 95 percent / CH2Cl2 / 15 h / -45 °C
11: 63 percent / Burgess' reagent
12: 100 percent / pyridine
13: 65 percent / OsO4
14: DBU / toluene / 2 h / 105 °C
15: 75 percent / pyridine, DMAP / 24 h / 25 °C
16: 100 percent / HF*pyridine / acetonitrile / 11 h / 0 °C
17: tetrahydrofuran / 0.17 h / -78 °C
18: tetrapropylammonium perruthenate, NMO, molecular sieves / CH2Cl2 / 0.25 h / 25 °C
19: 1.) t-BuOK, 2.) benzeneseleninic anhydride, 3.) t-BuOK
20: pyridine, DMAP / 20 h / 25 °C
21: 94 percent / TASF / tetrahydrofuran / 1 h / 25 °C
22: 1.) LHMDS / 1.) THF, 2.) THF, 0 deg C, 1 h
23: HF, pyridine / acetonitrile / 1 h / 0 °C
With
pyridine; dmap; potassium permanganate; potassium dihydrogenphosphate; osmium(VIII) oxide; N-methyl-2-indolinone; molecular sieve; tetrapropylammonium perruthennate; Burgess Reagent; benzeneseleninic anhydride; hydrogen fluoride; potassium tert-butylate; tris(dimethylamino)sulfonium trimethylsilyldifluoride; tetra-(n-butyl)ammonium iodide; (2E)-3-(4-hydroxyphenyl-3-methoxyphenyl)-1-phenylprop-2-en-1-one; toluene-4-sulfonic acid; pyridine hydrogenfluoride; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; lithium diisopropyl amide;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;