Synthesis of Dragmacidin D

C27H21BrF3N7O4
Principal investigator | Brian M. Stoltz |
---|---|
Publication year | 2002 |
Synthesis type | Total |
Number of steps | 21 (3 parts) |
References |
Part 1 of 3
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- NaH
- TMS(CH2)2OCH2Cl
THF
0 °C to RT, 6.5 h, 92%

- t-BuLi
- i-PrOBpin
THF
-78 °C, 105 min, 74%



Pd/C,
H2
1 atm
PhH
RT, 60 min, 99%

NBS
THF
RT, 5 min, 92%

- t-BuLi
- i-PrOBpin
THF
-78 °C, 75 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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Pyr.HF
THF
0 °C, 90 min



Dess-Martin Periodinane
CH2Cl2
RT, 5 min, 98% (2 steps)

KOH
EtOH
40 °C, 2 h

LiBF4
H2O, MeCN
70 °C, 90 min, 99% (2 steps)

SnCl2.2H2O
EtOAc
80 °C, 3 h

TMSI
MeCN
50 °C, 2 h, 80% (2 steps)

- NH2CN
- CF3CO2H
EtOH
60 °C, 3 h, 86%
