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%
