Multi-step reaction with 14 steps
1.1: PhNMe2 / 6 h / Heating
2.1: 82 percent / K2CO3 / acetone / Heating
3.1: 81 percent / HCl / 2 h / Heating
4.1: 72 percent / toluene / 24 h / Heating
5.1: 74 percent / OsO4; NMO / acetone / 20 °C
6.1: 69 percent / aq. NaIO4 / 2-methyl-propan-2-ol / 20 °C
7.1: CHCl3
8.1: CHCl3 / 10 h / 0 - 20 °C
9.1: 81 percent / HCl / diethyl ether / 48 h / 0 - 20 °C
10.1: Pb(OAc)4 / CH2Cl2; methanol / 0.25 h
10.2: H2 / 20percent Pd(OH)2/C / ethanol / 2585.81 Torr
11.1: Et3N / tetrahydrofuran / 20 °C
12.1: 96 percent / LiBH4 / tetrahydrofuran / 8 h / 0 - 20 °C
13.1: 96 percent / NH2OH*HCl; Et3N / propan-2-ol; H2O / 24 h / Heating
14.1: 87 percent / 2,6-lutidine / 1,2-dichloro-ethane
With
2,6-dimethylpyridine; lead(IV) acetate; hydrogenchloride; sodium periodate; osmium(VIII) oxide; lithium borohydride; N-methyl-2-indolinone; hydroxylamine hydrochloride; potassium carbonate; N,N-dimethyl-aniline; triethylamine;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; water; 1,2-dichloro-ethane; isopropyl alcohol; acetone; toluene; tert-butyl alcohol;
1.1: Claisen rearrangement;
DOI:10.1039/b008970m