Multi-step reaction with 13 steps
1.1: pyridine; DMAP / 0.33 h / 20 °C
2.1: BF3*Et2O / CH2Cl2 / 0.33 h / 20 °C
3.1: K2CO3 / methanol / 2 h / 20 °C
4.1: pyridine / CH2Cl2 / 1 h
5.1: 18-crown-6 / dimethylformamide / 4 h
6.1: LiOH / methanol
7.1: Et3N / CH2Cl2 / 0.33 h / -78 °C
8.1: mCPBA / CH2Cl2 / -42 °C
9.1: 21 percent / 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem molecular sieves; triflic anhydride / toluene; CH2Cl2 / 0.25 h / -78 °C
10.1: 95 percent / pyridinium hydrofluoride / tetrahydrofuran
11.1: 74 percent / triflic anhydride; 4 Angstroem molecular sieves / CH2Cl2; diethyl ether / 0.25 h / -78 °C
12.1: 90 percent / pyridinium hydrofluoride / tetrahydrofuran / 1 h
13.1: NaH / dimethylformamide / 0.08 h
13.2: 97 percent / dimethylformamide / 0.33 h
With
pyridine; dmap; lithium hydroxide; 2,6-di-tert-butyl-4-methylpyridine; 18-crown-6 ether; trifluoromethylsulfonic anhydride; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium hydride; potassium carbonate; pyridine hydrogenfluoride; triethylamine; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;
1.1: Acetylation / 2.1: Substitution / 3.1: Hydrolysis / 4.1: sulphonation / 5.1: Esterification / 6.1: Hydrolysis / 7.1: silylation / 8.1: Oxidation / 9.1: Condensation / 10.1: desilylation / 11.1: Condensation / 12.1: desilylation / 13.1: Metallation / 13.2: Methylation;
DOI:10.1021/ja992513f