Synthesis of Marinopyrrole B
C22H11BrCl4N2O4
Principal investigator | Derrick L. J. Clive |
---|---|
Publication year | 2013 |
Synthesis type | Total |
Number of steps | 18 (linear) |
References |
Part 1 of 1
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+
SO2Cl2
CHCl3
Reflux, 30 h, 81%
NaOMe
MeOH
0 °C to RT, 13 h, 91%
NBS
MeCN
RT, 14 h, 98%
- O3
- Me2S
CH2Cl2, MeOH
-78 °C to RT, 7 h, 91%
- NaH
- AllylBr
DMF
-42 °C to RT, 2 h, 69%
- O3
- Ph3P
CH2Cl2, MeOH
-78 °C to RT, 14 h
i-Pr2NEt,
TsCl,
DMAP
CH2Cl2
0 °C to RT, 24 h, 98%
i-Bu2AlH
CH2Cl2
0 °C to RT, 10.5 h, 100%
IBX
DMSO
70 °C, 15 h, 87%
IBX
DMSO
70 °C, 29 h
KOH
MeOH, THF
RT, 60 min, 27% (4 steps)
NCS
MeOH
35 °C, 15.5 h, 76%
BBr3
CH2Cl2
-78 °C, 50 min, 88%