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Named reactions

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Dragmacidin D

Chemical structure of Dragmacidin_D
C27H21BrF3N7O4
Author Brian M. Stoltz
Publication year 2002
Synthesis type Total synthesis
Number of steps 21 (3 parts)
Reference

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
VinylMgBr
THF
-40 °C, 4 h, 33 %

See the Bartoli Indole Synthesis
Chemical structure
  1. NaH
  2. TMS(CH2)2OCH2Cl
THF
0 °C to RT, 6.5 h, 92 %
Chemical structure
  1. t-BuLi
  2. i-PrOBpin
THF
-78 °C, 105 min, 74 %
Chemical structure
+
Chemical structure
Na2CO3, Pd(PPh3)4
PhH, MeOH, H2O
80 °C, 2 h, 83 %

See the Suzuki Coupling
Chemical structure
H2, Pd/C
1 atm
PhH
RT, 60 min, 99 %
Chemical structure
NBS
THF
RT, 5 min, 92 %
Chemical structure
  1. t-BuLi
  2. i-PrOBpin
THF
-78 °C, 75 min, 73 %
Chemical structure

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Part 2 of 3
Chemical structure
TsCl, KOH, n-Bu4N+ HSO4-
PhMe, H2O
RT, 4 h, 98 %
Chemical structure
Hg(OAc)2, HClO4
AcOH, H2O
RT, 24 h, 99 %
Chemical structure
  1. BH3.THF
  2. H2O
THF
RT, 60 min, 85 %
Chemical structure
+
Chemical structure
Na2CO3, Pd(PPh3)4
PhH, MeOH, H2O
RT, 72 h, 71 %

See the Suzuki Coupling
Chemical structure

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Part 3 of 3
Chemical structure
+
Chemical structure
Na2CO3, Pd(PPh3)4
PhH, MeOH, H2O
50 °C, 72 h, 82 %

See the Suzuki Coupling
Chemical structure
Pyr.HF
THF
0 °C, 90 min
Chemical structure
Dess-Martin Periodinane
CH2Cl2
RT, 20 min, 86 % (2 steps)

See the Dess-Martin Oxidation
Chemical structure
Et3N
MeNO2
RT, 15 h

See the Henry Reaction
Chemical structure
Dess-Martin Periodinane
CH2Cl2
RT, 5 min, 98 % (2 steps)
Chemical structure
KOH
EtOH
40 °C, 2 h
Chemical structure
LiBF4
MeCN, H2O
70 °C, 90 min, 99 % (2 steps)
Chemical structure
SnCl2.2H2O
EtOAc
80 °C, 3 h
Chemical structure
TMSI
MeCN
50 °C, 2 h, 80 % (2 steps)
Chemical structure
  1. NH2CN
  2. CF3CO2H
EtOH
60 °C, 3 h, 86 %
Chemical structure

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