Synthesis of Murrayazoline

C23H25NO
Principal investigator | Noritaka Chida |
---|---|
Publication year | 2008 |
Synthesis type | Total |
Number of steps | 22 (3 parts) |
References |
Part 1 of 3
+

Et3N,
TsCl
CH2Cl2
0 °C, 4 h

NIS
DMF
0 °C to RT, 60 min, 76% (2 steps)




NaOMe
MeOH
Reflux, 8 h

MeOCH2Cl,
NaH
DMF
0 °C to RT, 90 min, 92% (2 steps)

Part 2 of 3


HCl
H2O, THF
RT, 12 h, 74% (2 steps)

MeLi
Et2O
-78 °C, 60 min, 92%


MeLi
Et2O
-78 °C, 2 h, 64%

TMSN3,
TsOH,
BF3.OEt2
PhH
0 °C, 30 min

Me3O+BF4-,
CuSO4
CH2Cl2, H2O
0 °C to RT, 14 h, 61% (2 steps)

TMSCl,
TMS2NK,
Et3N
THF
-78 °C, 40 min


(TMSOCH2)2,
TMSOTf
CH2Cl2
-78 to -15 °C, 90 min, 99%

LiAlH4
THF
0 °C, 2 h, 87%

Part 3 of 3
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Sc(OTf)3
Sealed tube
DCE, H2O
120 °C, 36 h, 73%
See the Friedel-Crafts Alkylation
See the Michael Addition

DMAP,
Et3N,
Tf2O
CH2Cl2
0 °C, 60 min, 94%


