Synthesis of Cortistatin A

Structure of Cortistatin A

C30H36N2O3

Principal investigatorMatthew D. Shair
Publication year2008
Synthesis typeTotal
Number of steps 25 (linear)
References
J. Am. Chem. Soc. 2008, 130, 16864.
Part 1 of 1
intermediate structure + intermediate structure
NaH
DMSO
RT, 21 h, 63%
"The starting material was obtained in two steps from the Hajos-Parrish ketone."
intermediate structure
TBSOTf, 2,6-Lutidine
CH2Cl2
0 °C, 2 h
intermediate structure
Pd/C, H2
EtOAc
RT, 20 h
intermediate structure
NaHCO3, mCPBA, HF
PhMe, THF
-10 to 0 °C, 66% (3 steps)
See the Rubottom Oxidation
intermediate structure
MeO(CH2)2OCH2Cl, i-Pr2NEt
DCE
80 °C, 13 h, 88%
intermediate structure
Pyr.TsOH
Acetone, H2O
60 °C, 5 h
intermediate structure
NaOMe
MeOH
70 °C, 2 h, 49% (2 steps)
See the Aldol Addition
intermediate structure
SOCl2, Pyr
CH2Cl2
10 °C, 30 min
intermediate structure
TMS2NNa, PhNTf2
THF
-78 to 0°C, 3 h
intermediate structure + intermediate structure
Pd(PPh3)4
THF
RT, 30 min, 62% (3 steps)
See the Kumada-Corriu Coupling
intermediate structure
CHBr3, KOt-Bu
Syringe pump
Hexane(s)
0 °C, 2 h
intermediate structure
TASF
DMF
80 °C, 30 min, 66% (2 steps)
intermediate structure + intermediate structure
Pd(PPh3)4, K2CO3
H2O, THF
80 °C, 5 h, 84%
See the Suzuki Coupling
intermediate structure
(DHQD)2PHAL, K2OsO2(OH)4, K3Fe(CN)6, MsNH2, K2CO3
H2O, t-BuOH
See the Sharpless Asymmetric Dihydroxylation
intermediate structure
Et3N, Ac2O
CH2Cl2
RT, 18 h, 51% (2 steps)
intermediate structure
Pyr.HF
THF
RT, 5 min
intermediate structure
Dess-Martin Periodinane
CH2Cl2
RT, 60 min
See the Dess-Martin Oxidation
intermediate structure
ZnBr2, Me2NH
MeCN
50 °C, 40 min, 65% (3 steps)
See the Prins Reaction
intermediate structure
n-Bu4N+ F-
THF
70 °C, 4 h, 70%
intermediate structure
n-Pr4N+ RuO4-, NMO
CH2Cl2
RT, 2.5 h, 100%
See the Ley-Griffith Oxidation
intermediate structure
K2CO3
MeOH
RT, 30 min, 82%
intermediate structure
NH2NH2, Et3N
Sealed tube
EtOAc
80 °C, 6 h
intermediate structure
I2
THF
RT, 5 min
See the Barton Vinyl Iodide Synthesis
intermediate structure + intermediate structure
Pd(PPh3)4, LiCl, CuCl
DMSO
60 °C, 60 min, 61% (3 steps)
See the Stille Coupling
intermediate structure
Special reagent
Et3N
THF
60 °C, 9 h, 20%
intermediate structure
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