Synthesis of Zaragozic Acid C
C40H50O14
Principal investigator | David A. Evans |
---|---|
Publication year | 1994 |
Synthesis type | Total |
Number of steps | 29 (3 parts) |
References |
Part 1 of 3
+
2,6-Lutidine,
TBSOTf
CH2Cl2
0 °C, 60 min
LiBH4
MeOH, THF
0 °C, 3.5 h
Part 2 of 3
Pyr.TsOH,
2,2-Dimethoxypropane
PhH
98%
""This iodide was readily prepared from intermediates previously reported by us""
Part 3 of 3
+
+
+
TsOH,
Cyclopentanone dimethyl acetal
PhH
65 °C, 12 h, 85%
- TMS2NLi
- TMSCl
THF
-78 to 0 °C, 60 min, 97%
- O3 , Pyr
- Me2S
CH2Cl2
-78 °C to RT, 4 h
N,N'-diisopropyl-O-tert-butylisourea
CH2Cl2
24 h, 91% (3 steps)
t-BuLi
Et2O, Hexane(s)
-78 °C, 20 min, 73%
DDQ
CH2Cl2
60 min
Ac2O,
DMAP
PhH, Pyr
90% (2 steps)
H2O
CH2Cl2, CF3CO2H
N,N'-diisopropyl-O-tert-butylisourea
CH2Cl2
24 h, 52% (2 steps)
H2,
Pd/C
50 atm
AcOH, MeOH
20 h, 96%
n-Bu4N+ F-
THF
0 °C, 15 min, 99%
CF3CO2H
CH2Cl2
24 h, 99%