Synthesis of Aigialomycin D
C18H22O6
Principal investigator | Joanne E. Harvey |
---|---|
Publication year | 2009 |
Synthesis type | Total |
Number of steps | 20 (3 parts) |
References |
Part 1 of 3
- NaH
- n-BuLi
THF
-78 °C to Reflux, 51 h, 40%
Ac2O,
Et3N
CH2Cl2
RT, 12 h, 98%
Part 2 of 3
+
HCl
Acetone, MeOH
Reflux, 8 h, 55%
TsCl
Pyr
0 °C to RT, 15 h, 84%
Zn,
AcOH
MeOH
Reflux, 8 h
Cyclohexene,
NaBH4,
CuCl
MeOH
-78 °C, 60 min, 96%
LiAlH4
Et2O
-10 °C, 10 min, 97%
MsCl,
Et3N,
DMAP
CH2Cl2
0 °C to RT, 12 h, 97%
KSAc
DMF
0 °C to RT, 12 h, 90%
Part 3 of 3
+
+
K2CO3
MeOH
RT, 12 h, 86%
NaH,
MeOCH2Cl
DMF
0 °C to RT, 2 h, 74%
KOH
H2O, MeOH
90 °C, 48 h, 98%
mCPBA
CH2Cl2
0 °C to RT, 2 h, 84%
HCl
H2O, MeOH
RT, 3 d, 85%