Multi-step reaction with 11 steps
1: 70 percent / HMPA; LDA / -78 °C
2: 90 percent / imidazole / dimethylformamide
3: 86 percent / DIBAL-H / diethyl ether / -78 °C
4: (COCl)2; Et3N; DMSO / CH2Cl2 / -65 - -55 °C
5: LiCl; i-Pr2NEt / acetonitrile
6: 95 percent / DIBAL-H / diethyl ether / -78 °C
7: 76.5 percent / Ti(O-i-Pr)4; D-(-)-diisopropyl tartrate; t-BuOOH
8: 72.4 percent / diethyl ether / -20 - 0 °C
9: 84.4 percent / Et3N; DMAP / CH2Cl2
10: 97.7 percent / pyridine
11: 76.4 percent / NaN3 / dimethylformamide
With
1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium azide; oxalyl dichloride; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; lithium diisopropyl amide;
In
pyridine; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
1: Alkylation / 2: Substitution / 3: Reduction / 4: Oxidation / 5: Condensation / 6: Reduction / 7: Epoxidation / 8: Ring cleavage / 9: Substitution / 10: Mesylation / 11: Substitution;
DOI:10.1039/a907922j