Synthesis of Cortistatin A

C30H36N2O3
Principal investigator | Matthew D. Shair |
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Publication year | 2008 |
Synthesis type | Total |
Number of steps | 25 (linear) |
References |
Part 1 of 1
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NaH
DMSO
RT, 21 h, 63%
"The starting material was obtained in two steps from the Hajos-Parrish ketone."

TBSOTf,
2,6-Lutidine
CH2Cl2
0 °C, 2 h

Pd/C,
H2
EtOAc
RT, 20 h


MeO(CH2)2OCH2Cl,
i-Pr2NEt
DCE
80 °C, 13 h, 88%

Pyr.TsOH
Acetone, H2O
60 °C, 5 h


SOCl2,
Pyr
CH2Cl2
10 °C, 30 min

TMS2NNa,
PhNTf2
THF
-78 to 0°C, 3 h



CHBr3,
KOt-Bu
Syringe pump
Hexane(s)
0 °C, 2 h

TASF
DMF
80 °C, 30 min, 66% (2 steps)



(DHQD)2PHAL,
K2OsO2(OH)4,
K3Fe(CN)6,
MsNH2,
K2CO3
H2O, t-BuOH

Et3N,
Ac2O
CH2Cl2
RT, 18 h, 51% (2 steps)

Pyr.HF
THF
RT, 5 min



n-Bu4N+ F-
THF
70 °C, 4 h, 70%


K2CO3
MeOH
RT, 30 min, 82%

NH2NH2,
Et3N
Sealed tube
EtOAc
80 °C, 6 h





Et3N
THF
60 °C, 9 h, 20%
