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Named reactions

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Chlorodysinosin A

"This paper is dedicated to Professor K. C. Nicolaou, chemist extraordinaire, on the occasion of his 60th birthday."

Chemical structure of Chlorodysinosin_A
C26H43ClN6O10S
Author Stephen Hanessian
Publication year 2006
Synthesis type Total synthesis
Number of steps 27 (2 parts)
References

Browse hundreds of other total syntheses.

Part 1 of 2
Chemical structure
NaN3, NH4Cl
2-Methoxyethanol, H2O
Reflux, 24 h

Selectivity : 50:50
Chemical structure
+
Chemical structure
TBSCl, DMAP
CH2Cl2, Et3N
0 °C, 2 h, 75% (2 steps)
Chemical structure
+
Chemical structure
Ph3P
MeCN
RT to 50 °C, 20 h, 90%
Chemical structure
t-BuSOCl, Et3N
CH2Cl2
0 °C, 2 h
Chemical structure
mCPBA
CH2Cl2
0 °C, 60 min, 88% (2 steps)
Chemical structure
CeCl3.7H2O
MeCN
90 °C, 72 h, 80%
Chemical structure
TfOH, PhOMe
CH2Cl2
RT, 18 h
Chemical structure + Chemical structure
PyBOP, 2,6-Lutidine
CH2Cl2
RT, 18 h, 77% (2 steps)
Chemical structure
CrO3, HIO4
MeCN, H2O
0 °C, 30 min, 78%

See the Jones Oxidation
Chemical structure

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Part 2 of 2
Chemical structure
+
Chemical structure
TMS2NLi
THF
-78 °C, 20 min, 85%
Chemical structure
HCO2H
RT, 5 h
Chemical structure
PhMe
Reflux, 90 min
Chemical structure
  1. TMS2NLi
  2. ClCO2Bn
THF
-78 °C, 90 min, 82% (3 steps)
Chemical structure
LiBHEt3
THF
-78 °C, 60 min
Chemical structure
Ac2O, DMAP
CH2Cl2, Et3N
RT, ON, 80% (2 steps)
Chemical structure
SnBr4
CH2Cl2
-78 °C, 5 min, 60%

See the Prins Reaction
Chemical structure
DBU
80 °C, 4 h, 70%
Chemical structure
mCPBA
CH2Cl2
RT, 2 h

See the Prilezhaev Reaction
Chemical structure
CF3CO2H
THF, H2O
RT, ON, 75-79% (2 steps)
Chemical structure
MeOCH2Cl, i-Pr2NEt
CH2Cl2
RT, 18 h, 98%
Chemical structure
H2, Pd(OH)2
1 atm
MeOH
RT, 3 h, 95%
Chemical structure + Chemical structure
DEPBT, 2,6-Lutidine
CH2Cl2
0 °C, 4 h, 57%
Chemical structure
MeSnOH
DCE
75 °C, 48 h, 78%
Chemical structure + Chemical 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).
Chemical structure
n-Bu4N+ F-
THF
0 °C, 15 min, 85%
Chemical structure
Pyr.SO3, n-Bu2SnO
CH2Cl2
RT, 18 h
Chemical structure
CF3CO2H
CH2Cl2
RT, 6 h, 38% (2 steps)
Chemical structure

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