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1) NaH
2) RX

1) Hg(OAc)2, ROH
2) NaBH4

xs HX, heat

O2 (slow)

MCPBA

*
1) Br2, H2O
2) NaOH
Enantioselective epoxidation
(CH3)3COOH, DET

1) NaOR
2) H3O+

1) NaCN
2) H3O+

1) NaSR
2) H3O+

1) RMgBr
2) H3O+

1) LiAlH4
2) H3O+

HX

[H+], H2O

[H+], ROH

NaSH

NaOH/H2O, Br2

HCl, Zn

1) NaOH
2) RX

MeX

H2O2

NaIO4