Synthesis of Chlorodysinosin A

C26H43ClN6O10S
Principal investigator | Stephen Hanessian |
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Publication year | 2006 |
Synthesis type | Total |
Number of steps | 27 (2 parts) |
References |
Part 1 of 2
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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
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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)
