Synthesis of Dragmacidin D

Structure of Dragmacidin D

C27H21BrF3N7O4

Principal investigatorBrian M. Stoltz
Publication year2002
Synthesis typeTotal
Number of steps 21 (3 parts)
References
J. Am. Chem. Soc. 2002, 124, 13179.
Part 1 of 3
intermediate structure
VinylMgBr
THF
-40 °C, 4 h, 33%
See the Bartoli Indole Synthesis
intermediate structure
  1. NaH
  2. TMS(CH2)2OCH2Cl
THF
0 °C to RT, 6.5 h, 92%
intermediate structure
  1. t-BuLi
  2. i-PrOBpin
THF
-78 °C, 105 min, 74%
intermediate structure + intermediate structure
Pd(PPh3)4, Na2CO3
H2O, MeOH, PhH
80 °C, 2 h, 83%
See the Suzuki Coupling
intermediate structure
Pd/C, H2
1 atm
PhH
RT, 60 min, 99%
intermediate structure
NBS
THF
RT, 5 min, 92%
intermediate structure
  1. t-BuLi
  2. i-PrOBpin
THF
-78 °C, 75 min, 73%
intermediate structure
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Part 2 of 3
intermediate structure
KOH, TsCl, n-Bu4N+ HSO4-
H2O, PhMe
RT, 4 h, 98%
intermediate structure
Hg(OAc)2, HClO4
AcOH, H2O
RT, 24 h, 99%
intermediate structure
  1. BH3.THF
  2. H2O
THF
RT, 60 min, 85%
intermediate structure + intermediate structure
Na2CO3, Pd(PPh3)4
H2O, MeOH, PhH
RT, 72 h, 71%
See the Suzuki Coupling
intermediate structure
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Part 3 of 3
intermediate structure + intermediate structure
Na2CO3, Pd(PPh3)4
H2O, MeOH, PhH
50 °C, 72 h, 82%
See the Suzuki Coupling
intermediate structure
Pyr.HF
THF
0 °C, 90 min
intermediate structure
Dess-Martin Periodinane
CH2Cl2
RT, 20 min, 86% (2 steps)
See the Dess-Martin Oxidation
intermediate structure
Et3N
MeNO2
RT, 15 h
See the Henry Reaction
intermediate structure
Dess-Martin Periodinane
CH2Cl2
RT, 5 min, 98% (2 steps)
intermediate structure
KOH
EtOH
40 °C, 2 h
intermediate structure
LiBF4
H2O, MeCN
70 °C, 90 min, 99% (2 steps)
intermediate structure
SnCl2.2H2O
EtOAc
80 °C, 3 h
intermediate structure
TMSI
MeCN
50 °C, 2 h, 80% (2 steps)
intermediate structure
  1. NH2CN
  2. CF3CO2H
EtOH
60 °C, 3 h, 86%
intermediate structure
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