Synthesis of Dragmacidin F

C25H20BrN7O3
Principal investigator | Brian M. Stoltz |
---|---|
Publication year | 2004 |
Synthesis type | Total |
Number of steps | 25 (3 parts) |
References |
Part 1 of 3
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Amberlyst 15
Dean-Stark
DMF, PhH
Reflux, 16 h, 99%

DMAP,
Et3N,
TBSCl
DMF
-20 to -5 °C, 2.5 h, 69%

H2Cr2O7.2Pyr,
Celite
4 Å MS
MeCN
45 °C, 24 h, 91%


Pd/C,
H2
1 atm
MeOH
0 °C, 7 h, 99%

CDI,
NHMeOMe.HCl
CH2Cl2
RT, 3.5 h, 93%



Pd(OAc)2
AcOH, DMSO, t-BuOH
60 °C, 10 h, 74%

Pd/C,
H2
1 atm
EtOAc
RT, 30 min, 99%


NBS
THF
0 °C to RT, 15 min, 96%

- n-BuLi
- i-PrOBpin
THF
-78 °C, 15 min, 73%

Part 2 of 3
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KOH,
TsCl,
n-Bu4N+ HSO4-
H2O, PhMe
RT, 4 h, 98%

Hg(OAc)2,
HClO4
AcOH, H2O
RT, 24 h, 99%

- BH3.THF
- H2O
THF
RT, 60 min, 85%



Part 3 of 3
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LiBF4
H2O, MeCN
45-50 °C, 31 h, 98%


NH2OH.HCl,
NaOAc
H2O, MeOH
RT, 8 h, 98%

n-Bu4N+ Br-,
TsCl,
KOH
H2O, PhMe
0 °C, 2 h, 98%


K2CO3
H2O, THF
RT, 10 min, 96% (2 steps)

TMSI
MeCN
60 °C, 48 h, 95%

NaOH,
NH2CN
H2O
60 °C, 2 h, 86%
