1: NaBH4 2: protected as tetrahydropyranyl ether 3: 84 percent / TBAF 4: 98 percent / deacylation 5: 73 percent / triphenylphosphine, diethylazodicarboxylate / tetrahydrofuran / 0.08 h / Ambient temperature 6: diisobutyl aluminum hydride 7: 2.) aq. acetic acid View Scheme

Multi-step reaction with 6 steps 1: NaBH4 2: protected as tetrahydropyranyl ether3: 84 percent / TBAF4: 98 percent / deacylation5: 73 percent / triphenylphosphine, diethylazodicarboxylate / tetrahydrofuran / 0.08 h / Ambient temperature6: diisobutyl aluminum hydride  

Multi-step reaction with 4 steps 1: TiCl4 / CH2Cl2 2: H2, Lindlar catalyst / 0.83 h3: pyridine, DMAP4: PdCl2(MeCN)2  

With  dichloro bis(acetonitrile) palladium(II) in  tetrahydrofuran 2 h;  Ambient temperature;   

With  sodium tetrahydroborate