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Named reactions

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Dragmacidin F

Chemical structure of Dragmacidin_F
C25H20BrN7O3
Author Brian M. Stoltz
Publication year 2004
Synthesis type Total synthesis
Number of steps 25 (3 parts)
References

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
Amberlyst ® 15
Dean-Stark
PhH, DMF
Reflux, 16 h, 99%
Chemical structure
TBSCl, Et3N, DMAP
DMF
-20 to -5 °C, 2.5 h, 69%
Chemical structure
H2Cr2O7.2Pyr, Celite ®
4 Å MS
MeCN
45 °C, 24 h, 91%
Chemical structure
Ph3P+CH3 Br-, KOt-Bu
THF
65 °C, 2 h, 76%

See the Wittig Reaction
Chemical structure
H2, Pd/C
1 atm
MeOH
0 °C, 7 h, 99%
Chemical structure
CDI, NHMeOMe.HCl
CH2Cl2
RT, 3.5 h, 93%
Chemical structure + Chemical structure
THF
-78 to 0 °C, 30 min, 71%

See the Weinreb Ketone Synthesis
Chemical structure
Pd(OAc)2
DMSO, t-BuOH, AcOH
60 °C, 10 h, 74%
Chemical structure
H2, Pd/C
1 atm
EtOAc
RT, 30 min, 99%
Chemical structure
NaH, MeI
THF
0 °C to RT, 60 min, 96%

See the Williamson Ether Synthesis
Chemical structure
NBS
THF
0 °C to RT, 15 min, 96%
Chemical structure
  1. n-BuLi
  2. i-PrOBpin
THF
-78 °C, 15 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
H2O, AcOH
RT, 24 h, 99%
Chemical structure
  1. BH3.THF
  2. H2O
THF
RT, 60 min, 85%
Chemical structure + Chemical structure
Pd(PPh3)4, Na2CO3
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
Pd(PPh3)4, Na2CO3
PhH, MeOH, H2O
50 °C, 2.5 d, 77%

See the Suzuki Coupling
Chemical structure
LiBF4
MeCN, H2O
45-50 °C, 31 h, 98%
Chemical structure
Dess-Martin Periodinane
CH2Cl2
RT, 3 min, 90%

See the Dess-Martin Oxidation
Chemical structure
NH2OH.HCl, NaOAc
MeOH, H2O
RT, 8 h, 98%
Chemical structure
TsCl, KOH, n-Bu4N+ Br-
PhMe, H2O
0 °C, 2 h, 98%
Chemical structure
KOH, HCl
EtOH, H2O
0 to 60 °C, 13 h

See the Neber Rearrangement
Chemical structure
K2CO3
THF, H2O
RT, 10 min, 96% (2 steps)
Chemical structure
TMSI
MeCN
60 °C, 48 h, 95%
Chemical structure
NH2CN, NaOH
H2O
60 °C, 2 h, 86%
Chemical structure

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