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Named reactions

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Cortistatin A

"Dedicated to Professor E. J. Corey on the occasion of his 80th birthday."

Chemical structure of Cortistatin_A
C30H36N2O3
Author Phil S. Baran
Publication year 2008
Synthesis type Partial synthesis
Number of steps 19 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
  1. BH3.THF
  2. NaIO4, Acetone, H2O
THF
0 °C to RT, 4 h

"Prednisone [...] at $1.20/g possesses 70% of the carbon atoms and the corresponding, enantiopure chirality of [cortistatin A]"
Chemical structure
(CH2OH)2, TsOH
PhMe
Reflux, 60 min, 92% (2 steps)
Chemical structure
t-BuOOH, DBU
THF
RT, 72 h, 82%

See the Michael Addition
Chemical structure
  1. NaBH3CN, NH4OAc
  2. HCO2Et, Et3N
THF, MeOH
RT to 54 °C, 48 h, 73%
Chemical structure
n-Bu4N+ OAc-, Co(acac)2
PhH
90 °C, 24 h, 48%

The yield was 76 % brsm.
Chemical structure
  1. O2, Co(acac)2, PhSiH3
  2. TsOH
  3. K2CO3, MeOH
THF, HC(OMe)3
RT, 14 h, 63%

See the Mukaiyama Hydration
Three stage, one pot reaction.
Chemical structure
PhI(OAc)2, Br2
CH2Cl2
-30 °C, 10 h
Chemical structure
TMSCl, Imidazole
CH2Cl2
0 °C, 15 min, 57% (2 steps)
Chemical structure
DBU, LiCl
THF
RT, 24 h, 85%
Chemical structure
Reagent structure
SmI2
THF, DMPU
-72 °C to RT, 35 min
Chemical structure
Li2CO3, LiBr
DMF
60 °C, 60 min, 63% (2 steps)
Chemical structure
  1. AlH3
  2. K2CO3, MeOH
THF
RT, 13 h
Chemical structure
Ac2O, Et3N, DMAP
CH2Cl2
RT, 5 h, 89% (2 steps)
Chemical structure
MgBr2.OEt2, 2,6-Di-tert-butylpyridine
PhH
78 °C, 90 min
Chemical structure
  1. Pyr.TsOH
  2. K2CO3
MEK, H2O
90 °C to RT, 7 h, 82% (2 steps)
Chemical structure
NH2NH2, Et3N
EtOH
50 °C, 6 h
Chemical structure
I2, Et3N
THF
RT, 5 min

See the Barton Vinyl Iodide Synthesis
Chemical structure + Chemical structure
Pd(PPh3)4, CuCl, LiCl
DMSO
RT, 10 min, 53% (3 steps)

See the Stille Coupling
Chemical structure
Ni (Raney)
i-PrOH, H2O
50 °C, 60 min, 50%

The yield was 100 % brsm.
Chemical structure

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