Synthesis of Aigialomycin D

Structure of Aigialomycin D

C18H22O6

Principal investigatorJoanne E. Harvey
Publication year2009
Synthesis typeTotal
Number of steps 20 (3 parts)
References
Part 1 of 3
intermediate structure
  1. NaH
  2. n-BuLi
THF
-78 °C to Reflux, 51 h, 40%
intermediate structure
Ac2O, Et3N
CH2Cl2
RT, 12 h, 98%
intermediate structure
NBS, Bz2O2
CCl4
Reflux, 6 h, 71%
intermediate structure
Part 2 of 3
intermediate structure
HCl
Acetone, MeOH
Reflux, 8 h, 55%
intermediate structure
TsCl
Pyr
0 °C to RT, 15 h, 84%
intermediate structure
NaI
MEK
Reflux, 24 h, 99%
intermediate structure
Zn, AcOH
MeOH
Reflux, 8 h
intermediate structure + intermediate structure
MeOH
0 °C to RT, 12 h, 74% (2 steps)
See the Wittig Reaction
intermediate structure
NaBH4, CuCl, Cyclohexene
MeOH
-78 °C, 60 min, 96%
intermediate structure
LiAlH4
Et2O
-10 °C, 10 min, 97%
intermediate structure
MsCl, Et3N, DMAP
CH2Cl2
0 °C to RT, 12 h, 97%
intermediate structure
KSAc
DMF
0 °C to RT, 12 h, 90%
intermediate structure
Part 3 of 3
intermediate structure + intermediate structure
K2CO3
MeOH
RT, 12 h, 86%
intermediate structure
MeOCH2Cl, NaH
DMF
0 °C to RT, 2 h, 74%
intermediate structure
KOH
MeOH, H2O
90 °C, 48 h, 98%
intermediate structure + intermediate structure
Ph3P, DIAD
THF
0 °C to RT, 2.5 h, 94%
intermediate structure
mCPBA
CH2Cl2
0 °C to RT, 2 h, 84%
intermediate structure
Grubbs-Hoveyda catalyst (2nd gen.)
CH2Cl2
75 °C, 30 min, 86%
intermediate structure
KOH, CCl4
CH2Cl2, t-BuOH
RT to 35 °C, 32 min, 84%
intermediate structure
HCl
MeOH, H2O
RT, 3 d, 85%
intermediate structure