Synthesis of Marinopyrrole B

Structure of Marinopyrrole B

C22H11BrCl4N2O4

Principal investigatorDerrick L. J. Clive
Publication year2013
Synthesis typeTotal
Number of steps 18 (linear)
References
Chem. Commun. 2013, 49, 558.
Part 1 of 1
intermediate structure
SO2Cl2
CHCl3
Reflux, 30 h, 81%
intermediate structure
NaOMe
MeOH
0 °C to RT, 13 h, 91%
intermediate structure
NBS
MeCN
RT, 14 h, 98%
intermediate structure + intermediate structure
K2CO3
MeCN
Reflux, 42 h, 95%
See the Michael Addition
intermediate structure
  1. O3
  2. Me2S
CH2Cl2, MeOH
-78 °C to RT, 7 h, 91%
intermediate structure
  1. NaH
  2. AllylBr
DMF
-42 °C to RT, 2 h, 69%
intermediate structure
PhMe
Reflux, 16 h
See the Claisen Rearrangement
intermediate structure
  1. O3
  2. Ph3P
CH2Cl2, MeOH
-78 °C to RT, 14 h
intermediate structure
NH4OAc
AcOH
RT, 30 min, 61% (3 steps)
See the Paal-Knorr Pyrrole Synthesis
intermediate structure
i-Pr2NEt, TsCl, DMAP
CH2Cl2
0 °C to RT, 24 h, 98%
intermediate structure
i-Bu2AlH
CH2Cl2
0 °C to RT, 10.5 h, 100%
intermediate structure
IBX
DMSO
70 °C, 15 h, 87%
intermediate structure + intermediate structure
THF
0 °C, 4 h
See the Grignard Reaction
intermediate structure
IBX
DMSO
70 °C, 29 h
intermediate structure intermediate structure
CrO3, H2SO4
Acetone, H2O
0 °C, 4 h
See the Jones Oxidation
intermediate structure
KOH
MeOH, THF
RT, 60 min, 27% (4 steps)
intermediate structure
NCS
MeOH
35 °C, 15.5 h, 76%
intermediate structure
BBr3
CH2Cl2
-78 °C, 50 min, 88%
intermediate structure
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