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Named reactions

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Clavizepine

"Dedicated to Professor Emeritus Yasumitsu Tamura of Osaka University on the occasion of his 70th birthday."

Chemical structure of Clavizepine
C19H21NO4
Author Hiroyuki Ishibashi
Publication year 1994
Synthesis type Total synthesis
Number of steps 15 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
+
Chemical structure
SnCl4
CH2Cl2
RT, 30 min, 98 %

See the Friedel-Crafts Alkylation
Chemical structure
Zn
AcOH
Reflux, 5 h, 96 %
Chemical structure
+
Chemical structure
CuO, K2CO3
Pyr
Reflux, 20 h, 61 %

See the Ullmann Condensation
Chemical structure
  1. i-Pr2NLi
  2. O2
THF, HMPA
-78 °C to RT, 2 h, 63 %
Chemical structure
SnCl4
CH2Cl2
0 °C to RT, 7 h, 66 %

See the Bradsher Cyclization
Chemical structure
H2, Pd/C
6 atm
MeOH
RT, 7 d, 86 %
Chemical structure
BnBr, K2CO3
Acetone
Reflux, 2 h, 92 %

See the Williamson Ether Synthesis
Chemical structure
MeNH2
Sealed tube
MeOH
95 °C, 5 h, 92 %
Chemical structure
BH3.THF
THF
Reflux, 10 d
Chemical structure
+
Chemical structure
Et3N
CH2Cl2
0 °C to RT, 9 h, 97 % (2 steps)
Chemical structure
NaIO4
MeOH, H2O
0 °C to RT, 2.5 d

"Excellent yield"
Chemical structure
(CF3CO)2O
CH2Cl2
0 °C to RT, 2.5 d, 95 %

See the Pummerer Rearrangement
Chemical structure
Zn
AcOH
Reflux, 5 h, 92 %
Chemical structure
Red-Al
PhH
Reflux, 26 h, 62 %
Chemical structure
Ni (Raney)
EtOH
Reflux, 5 h, 93 %
Chemical structure

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