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Named reactions

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Murrayazoline

Chemical structure of Murrayazoline
C23H25NO
Author Noritaka Chida
Publication year 2008
Synthesis type Total synthesis
Number of steps 22 (3 parts)
Reference

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
TsCl, Et3N
CH2Cl2
0 °C, 4 h
Chemical structure
NIS
DMF
0 °C to RT, 60 min, 76% (2 steps)
Chemical structure + Chemical structure
Pd(PPh3)4, Na2CO3
PhH, EtOH, H2O
Reflux, 3 h, 99%

See the Suzuki Coupling
Chemical structure
  1. NaNO2, H2SO4
  2. CuBr, HBr
AcOH, H2O
0 to 80 °C, 14 h, 92%

See the Sandmeyer Reaction
Chemical structure
NaOMe
MeOH
Reflux, 8 h
Chemical structure
NaH, MeOCH2Cl
DMF
0 °C to RT, 90 min, 92% (2 steps)
Chemical structure

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Part 2 of 3
Chemical structure
Ph3P+CH2OMe Cl-, TMS2NK
PhMe
0 to 120 °C, 4 h

See the Wittig Reaction
Chemical structure
HCl
THF, H2O
RT, 12 h, 74% (2 steps)
Chemical structure
MeLi
Et2O
-78 °C, 60 min, 92%
Chemical structure
n-Pr4N+ RuO4-, NMO
4 Å MS
CH2Cl2
RT, 30 min, 85%

See the Ley-Griffith Oxidation
Chemical structure
MeLi
Et2O
-78 °C, 2 h, 64%
Chemical structure
TMSN3, TsOH, BF3.OEt2
PhH
0 °C, 30 min
Chemical structure
Me3O+ BF4-, CuSO4
CH2Cl2, H2O
0 °C to RT, 14 h, 61% (2 steps)
Chemical structure
TMS2NK, TMSCl, Et3N
THF
-78 °C, 40 min
Chemical structure
Pd(OAc)2
MeCN
RT, 4 h, 84% (2 steps)

See the Saegusa-Ito Oxidation
Chemical structure
(TMSOCH2)2, TMSOTf
CH2Cl2
-78 to -15 °C, 90 min, 99%
Chemical structure
LiAlH4
THF
0 °C, 2 h, 87%
Chemical structure

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Part 3 of 3
Chemical structure
+
Chemical structure
Reagent structure
Pd2(dba)3, NaOt-Bu
Sealed tube
PhMe
130 °C, 13 h, 59%

See the Buchwald-Hartwig Coupling
Chemical structure
Sc(OTf)3
Sealed tube
DCE, H2O
120 °C, 36 h, 73%

See the Michael Addition
See the Friedel-Crafts Alkylation
Chemical structure
Tf2O, Et3N, DMAP
CH2Cl2
0 °C, 60 min, 94%
Chemical structure
MeMgBr
Et2O
0 °C, 60 min, 77%

See the Grignard Reaction
Chemical structure
Reagent structure
Pd(OAc)2
Sealed tube
PhMe
120 °C, 20 h, 80%

See the Buchwald-Hartwig Coupling
Chemical structure

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