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Br2, FeBr3

SO3, H2SO4

dilute H2SO4, heat

HNO3, H2SO4

Cl-R, AlCl3

KMnO4, H2O, heat
H3O+

NBS (excess)

1.Zno, HCl
2.NaOH

1.NaOH, 70 oC
2.H3O+

1.Hg(OAc)2, H2O
2.NaBH4

1.BH3THF
2.H2O2, NaOH

Br2, H2O

NaOH

H2O

HBr

TsCl, pyr

1.NaH
2.CH3I

PCC, CH2Cl2

PCC, DCM

green
1.DMSO
2.NEt3
or DMP/DCM

H3O+

H3O+

2ROH, H3O+ (non-nucleophilic acid)

H2NR, weak acid (AcOH)

H-NR2 (2o amine), AcOH

LiAlH4/NaBH4, H3O+

LiAlH4/NaBH4, H3O+

LiAlH4/NaBH4, H3O+

1) R’-Li/R’-MgBr, 2) H3O+

ylide

1):PPh3, 2)NaH

Nuc:

CrO3, H2SO4, H2O

CrO3, H2SO4, H2O

1) KMnO4, H2O, heat, 2) H3O+

1) O=C=O, 2) H3O+

H2SO4, H2O

CH3OH, H2SO4

1) LiBH4 2) H3O+, or BH3 THF (only CA)

SOCl2, pyr

H2O, pyr

R’-OH, pyr

2 eq :NH3

(CH3)2CuLi

1) LiAlH4 2) H3O+

1) R’-MgBr 2) H3O+

H3O+ or 1) NaOH 2) H3O+

H3O+, heat

1) LiAlH4 2) H3O+

1) LiAlH4 2) H3O+

Br2, H3O+

Br2, NaOH

1.Br2, NaOH
2.H3O+

NaOH

NaOH, heat

1.NaOR
2.H3O+

LDA

1.LDA
2.R-X

LDA

NaH

1.NaOEt
2.R-X
3.H3O+, heat
peptide synthesis
DCC
protect amine
(Boc)2O
deprotect amine
TFA
protect CA
CH3OH, H2SO4
deprotect CA
HBr