dilithium tetrachlorocuprate in tetrahydrofuran T=-20°C; 14 h; Yield givenYields of byproduct given. Title compound not separated from byproducts;

1: NaBH4, Ce(III) chloride / methanol View Scheme

1: diethyl ether 2: NaBH4, Ce(III) chloride / methanol View Scheme

tetrabutyl ammonium fluoride in tetrahydrofuran Ambient temperature;

1: 1.) LDA / 1.) THF, -60 deg C, 10 min, 2.) THF, -60 deg C, 5 min 2: 10percent aq. KOH / methanol / 0.25 h / Ambient temperature 3: imidazole / dimethylformamide / Ambient temperature 4: DIBAL-H / toluene / 0.17 h / -60 °C 5: 4-dimethylaminopyridine / CH2Cl2 / 0 - 20 °C 6: tributyltin hydride / 7 h / 160 °C 7: n-Bu4NF / tetrahydrofuran / Ambient temperature View Scheme

1: 10percent aq. KOH / methanol / 0.25 h / Ambient temperature 2: imidazole / dimethylformamide / Ambient temperature 3: DIBAL-H / toluene / 0.17 h / -60 °C 4: 4-dimethylaminopyridine / CH2Cl2 / 0 - 20 °C 5: tributyltin hydride / 7 h / 160 °C 6: n-Bu4NF / tetrahydrofuran / Ambient temperature View Scheme

1: DIBAL-H / toluene / 0.17 h / -60 °C 2: 4-dimethylaminopyridine / CH2Cl2 / 0 - 20 °C 3: tributyltin hydride / 7 h / 160 °C 4: n-Bu4NF / tetrahydrofuran / Ambient temperature View Scheme

1: imidazole / dimethylformamide / Ambient temperature 2: DIBAL-H / toluene / 0.17 h / -60 °C 3: 4-dimethylaminopyridine / CH2Cl2 / 0 - 20 °C 4: tributyltin hydride / 7 h / 160 °C 5: n-Bu4NF / tetrahydrofuran / Ambient temperature View Scheme

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