Synthesis of Chlorodysinosin A
C26H43ClN6O10S
| Principal investigator | Stephen Hanessian |
|---|---|
| Publication year | 2006 |
| Synthesis type | Total |
| Number of steps | 27 (2 parts) |
| References |
Part 1 of 2
+
+
+
NaN3,
NH4Cl
H2O, 2-Methoxyethanol
Reflux, 24 h
+
TBSCl,
DMAP
CH2Cl2, Et3N
0 °C, 2 h, 75% (2 steps)
+
Ph3P
MeCN
RT to 50 °C, 20 h, 90%
t-BuSOCl,
Et3N
CH2Cl2
0 °C, 2 h
mCPBA
CH2Cl2
0 °C, 60 min, 88% (2 steps)
CeCl3.7H2O
MeCN
90 °C, 72 h, 80%
PhOMe,
TfOH
CH2Cl2
RT, 18 h
+
PyBOP,
2,6-Lutidine
CH2Cl2
RT, 18 h, 77% (2 steps)
Part 2 of 2
+
+
+
+
TMS2NLi
THF
-78 °C, 20 min, 85%
HCO2H
RT, 5 h
PhMe
Reflux, 90 min
- TMS2NLi
- ClCO2Bn
THF
-78 °C, 90 min, 82% (3 steps)
LiBHEt3
THF
-78 °C, 60 min
Ac2O,
DMAP
CH2Cl2, Et3N
RT, ON, 80% (2 steps)
DBU
80 °C, 4 h, 70%
CF3CO2H
H2O, THF
RT, ON, 75-79% (2 steps)
MeOCH2Cl,
i-Pr2NEt
CH2Cl2
RT, 18 h, 98%
Pd(OH)2,
H2
1 atm
MeOH
RT, 3 h, 95%
+
2,6-Lutidine,
DEPBT
CH2Cl2
0 °C, 4 h, 57%
MeSnOH
DCE
75 °C, 48 h, 78%
+
2,6-Lutidine,
PyBOP
DCE
0 °C, 4 h, 93%
"For the synthesis of this amine, see the synthesis of Dysinosin A by Stephen Hanessian (2002)."
n-Bu4N+ F-
THF
0 °C, 15 min, 85%
Pyr.SO3,
n-Bu2SnO
CH2Cl2
RT, 18 h
CF3CO2H
CH2Cl2
RT, 6 h, 38% (2 steps)