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Named reactions

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Cortistatin A

Chemical structure of Cortistatin_A
C30H36N2O3
Author Matthew D. Shair
Publication year 2008
Synthesis type Total synthesis
Number of steps 25 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
+
Chemical structure
NaH
DMSO
RT, 21 h, 63%

The starting material was obtained in two steps from the Hajos-Parrish ketone.
Chemical structure
TBSOTf, 2,6-Lutidine
CH2Cl2
0 °C, 2 h
Chemical structure
H2, Pd/C
EtOAc
RT, 20 h
Chemical structure
mCPBA, NaHCO3, HF
PhMe, THF
-10 to 0 °C, 66% (3 steps)

See the Rubottom Oxidation
Chemical structure
MeO(CH2)2OCH2Cl, i-Pr2NEt
DCE
80 °C, 13 h, 88%
Chemical structure
Pyr.TsOH
Acetone, H2O
60 °C, 5 h
Chemical structure
NaOMe
MeOH
70 °C, 2 h, 49% (2 steps)

See the Aldol Addition
Chemical structure
SOCl2, Pyr
CH2Cl2
10 °C, 30 min
Chemical structure
TMS2NNa, PhNTf2
THF
-78 to 0°C, 3 h
Chemical structure + Chemical structure
Pd(PPh3)4
THF
RT, 30 min, 62% (3 steps)

See the Kumada-Corriu Coupling
Chemical structure
CHBr3, KOt-Bu
Syringe pump
Hexane(s)
0 °C, 2 h
Chemical structure
TASF
DMF
80 °C, 30 min, 66% (2 steps)
Chemical structure + Chemical structure
Pd(PPh3)4, K2CO3
THF, H2O
80 °C, 5 h, 84%

See the Suzuki Coupling
Chemical structure
K2OsO2(OH)4, (DHQD)2PHAL, K3Fe(CN)6, K2CO3, MsNH2
t-BuOH, H2O

See the Sharpless Asymmetric Dihydroxylation
Chemical structure
Ac2O, Et3N
CH2Cl2
RT, 18 h, 51% (2 steps)
Chemical structure
Pyr.HF
THF
RT, 5 min
Chemical structure
Dess-Martin Periodinane
CH2Cl2
RT, 60 min

See the Dess-Martin Oxidation
Chemical structure
Me2NH, ZnBr2
MeCN
50 °C, 40 min, 65% (3 steps)

See the Prins Reaction
Chemical structure
n-Bu4N+ F-
THF
70 °C, 4 h, 70%
Chemical structure
n-Pr4N+ RuO4-, NMO
CH2Cl2
RT, 2.5 h, 100%

See the Ley-Griffith Oxidation
Chemical structure
K2CO3
MeOH
RT, 30 min, 82%
Chemical structure
NH2NH2, Et3N
Sealed tube
EtOAc
80 °C, 6 h
Chemical structure
I2
THF
RT, 5 min

See the Barton Vinyl Iodide Synthesis
Chemical structure + Chemical structure
Pd(PPh3)4, CuCl, LiCl
DMSO
60 °C, 60 min, 61% (3 steps)

See the Stille Coupling
Chemical structure
Reagent structure
Et3N
THF
60 °C, 9 h, 20%
Chemical structure

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