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HX
mark, no stereo

H3O+
mark, no stereo

X2, H2O
mark, anti

Hg(OAc)2, H2O/THF 2. NaBH4
mark, anti

BH3 THF 2. H2O2, NaOH
anti-mark, syn

OsO4, NMO
no regio, syn

H2, PD/C
no regio, syn

RCO3H
no regio, syn

OsO4, NMO or KMnO4
no regio, syn

CH2I2, ZnCu or CHCl3, base
no regio, syn

X2
no regio, anti

epoxisde —> H3O+
no regio, anti
NaNH2



H2, Lindlar cat

Li0 or Na0, NH3 (l)

X2

X2 (xs)

HgSO4, H2SO4/H2O

BH3 THF
H2O2, NaOH

HX

HX (xs)
