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Named reactions

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Marinopyrrole B

Chemical structure of Marinopyrrole_B
C22H11BrCl4N2O4
Author Derrick L. J. Clive
Publication year 2013
Synthesis type Total synthesis
Number of steps 18 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
SO2Cl2
CHCl3
Reflux, 30 h, 81%
Chemical structure
NaOMe
MeOH
0 °C to RT, 13 h, 91%
Chemical structure
NBS
MeCN
RT, 14 h, 98%
Chemical structure + Chemical structure
K2CO3
MeCN
Reflux, 42 h, 95%

See the Michael Addition
Chemical structure
  1. O3
  2. Me2S
CH2Cl2, MeOH
-78 °C to RT, 7 h, 91%
Chemical structure
  1. NaH
  2. AllylBr
DMF
-42 °C to RT, 2 h, 69%
Chemical structure
PhMe
Reflux, 16 h

See the Claisen Rearrangement
Chemical structure
  1. O3
  2. Ph3P
CH2Cl2, MeOH
-78 °C to RT, 14 h
Chemical structure
NH4OAc
AcOH
RT, 30 min, 61% (3 steps)

See the Paal-Knorr Pyrrole Synthesis
Chemical structure
TsCl, i-Pr2NEt, DMAP
CH2Cl2
0 °C to RT, 24 h, 98%
Chemical structure
i-Bu2AlH
CH2Cl2
0 °C to RT, 10.5 h, 100%
Chemical structure
IBX
DMSO
70 °C, 15 h, 87%
Chemical structure + Chemical structure
THF
0 °C, 4 h

See the Grignard Reaction
Chemical structure
IBX
DMSO
70 °C, 29 h
Chemical structure
+
Chemical structure
CrO3, H2SO4
Acetone, H2O
0 °C, 4 h

See the Jones Oxidation
Chemical structure
KOH
THF, MeOH
RT, 60 min, 27% (4 steps)
Chemical structure
NCS
MeOH
35 °C, 15.5 h, 76%
Chemical structure
BBr3
CH2Cl2
-78 °C, 50 min, 88%
Chemical structure

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