Multi-step reaction with 14 steps
1: 92 percent / Triton B
2: TiCl3, Et3N
3: c. HCl / CH2Cl2 / 70percent yield from INO 1110
4: 81 percent / BF3:Et2O / CH2Cl2 / Ambient temperature
5: LDA / tetrahydrofuran / 1.) -78 deg C, 2.) -20 deg C
6: CSA / CH2Cl2; methanol
7: DMSO, DCC / pyridine; trifluoroacetic acid; diethyl ether / 91percent yield from INO 1150
8: Zn(BH4)2 / diethyl ether / -78 °C
9: 86 percent / DMAP / pyridine
10: HgO, HgCl2 / H2O; acetonitrile
11: Zn(BH4)2 / diethyl ether / 91percent from INO 1240
12: 94 percent / Bu3P / tetrahydrofuran / 0 °C
13: 100 percent / PrSLi / hexamethylphosphoric acid triamide
14: SOCl2, pyridine / CH2Cl2
With
pyridine; hydrogenchloride; dmap; thionyl chloride; titanium(III) chloride; zinc(II) tetrahydroborate; tributylphosphine; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; N-benzyl-trimethylammonium hydroxide; lithium n-propylmercaptide; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; mercury dichloride; mercury(II) oxide; lithium diisopropyl amide;
In
tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; water; acetonitrile; trifluoroacetic acid;
DOI:10.1016/S0040-4039(00)99028-2