Synthesis of Chlorodysinosin A

Structure of Chlorodysinosin A

C26H43ClN6O10S

Principal investigatorStephen Hanessian
Publication year2006
Synthesis typeTotal
Number of steps 27 (2 parts)
References
Part 1 of 2
intermediate structure
NaN3, NH4Cl
2-Methoxyethanol, H2O
Reflux, 24 h
intermediate structure + intermediate structure
TBSCl, DMAP
CH2Cl2, Et3N
0 °C, 2 h, 75% (2 steps)
intermediate structure + intermediate structure
Ph3P
MeCN
RT to 50 °C, 20 h, 90%
intermediate structure
t-BuSOCl, Et3N
CH2Cl2
0 °C, 2 h
intermediate structure
mCPBA
CH2Cl2
0 °C, 60 min, 88% (2 steps)
intermediate structure
CeCl3.7H2O
MeCN
90 °C, 72 h, 80%
intermediate structure
TfOH, PhOMe
CH2Cl2
RT, 18 h
intermediate structure + intermediate structure
PyBOP, 2,6-Lutidine
CH2Cl2
RT, 18 h, 77% (2 steps)
intermediate structure
CrO3, HIO4
MeCN, H2O
0 °C, 30 min, 78%
See the Jones Oxidation
intermediate structure
Part 2 of 2
intermediate structure + intermediate structure
TMS2NLi
THF
-78 °C, 20 min, 85%
intermediate structure
HCO2H
RT, 5 h
intermediate structure
PhMe
Reflux, 90 min
intermediate structure
  1. TMS2NLi
  2. ClCO2Bn
THF
-78 °C, 90 min, 82% (3 steps)
intermediate structure
LiBHEt3
THF
-78 °C, 60 min
intermediate structure
Ac2O, DMAP
CH2Cl2, Et3N
RT, ON, 80% (2 steps)
intermediate structure
SnBr4
CH2Cl2
-78 °C, 5 min, 60%
See the Prins Reaction
intermediate structure
DBU
80 °C, 4 h, 70%
intermediate structure
mCPBA
CH2Cl2
RT, 2 h
intermediate structure
CF3CO2H
THF, H2O
RT, ON, 75-79% (2 steps)
intermediate structure
MeOCH2Cl, i-Pr2NEt
CH2Cl2
RT, 18 h, 98%
intermediate structure
H2, Pd(OH)2
MeOH
RT, 3 h, 95%
intermediate structure + intermediate structure
DEPBT, 2,6-Lutidine
CH2Cl2
0 °C, 4 h, 57%
intermediate structure
MeSnOH
DCE
75 °C, 48 h, 78%
intermediate structure + intermediate structure
PyBOP, 2,6-Lutidine
DCE
0 °C, 4 h, 93%
"For the synthesis of this amine, see the synthesis of Dysinosin A by Stephen Hanessian (2002)."
intermediate structure
n-Bu4N+ F-
THF
0 °C, 15 min, 85%
intermediate structure
Pyr.SO3, n-Bu2SnO
CH2Cl2
RT, 18 h
intermediate structure
CF3CO2H
CH2Cl2
RT, 6 h, 38% (2 steps)
intermediate structure