[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C@:8]([S:29]C([C@@]12C(C)(C)C(C)(CC1)C(=O)O2)=O)([CH2:26][CH2:27][CH3:28])[CH2:9][CH2:10][O:11]C(=O)C1C=C([N+]([O-])=O)C=C([N+]([O-])=O)C=1>CCOCC.C1COCC1>[SH:29][C@@:8]([CH3:7])([CH2:26][CH2:27][CH3:28])[CH2:9][CH2:10][OH:11]To a suspension of 0.28 g (7.5 mmol) of LiAlH4 in 10 ml of Et2O was added a solution of 1.3 g of (1S,3S)-3,5-dinitro-benzoic acid 3-methyl-3-(4,7,7-trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carbonylsulfanyl)-hexyl ester of step (b) in 10 ml of THF. The reaction mixture was stirred at room temperature overnight, quenched with 20 ml of water and filtered over Celite. The organic layer was separated, dried over MgSO4 and concentrated in vacuo. The residue was distilled (bulb to bulb, 0.06 Torr, up to 190° C.) and gave 100 mg (27%) of (S)-3-mercapto-3-methyl-hexan-1-ol in form of a colorless oil.
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