Synthesis of Spiroindimicin B

Structure of Spiroindimicin B

C23H17Cl2N3O2

Principal investigatorJonathan Sperry
Publication year2016
Synthesis typeTotal
Number of steps 14 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
NaH, n-Bu4N+ I-
THF
0 °C to RT, 3.5 h, 85%
intermediate structure
AgNO3, Pd(OAc)2, n-Bu4N+ Cl-, HCO2Na
NMP
RT, 3 h, 93%
See the Heck Coupling
intermediate structure
H2, Pd/C
1 atm
EtOAc
RT, 60 min, 99%
intermediate structure
Special reagent
AcOH
110 °C, 40 h, 75% (93% BRSM)
intermediate structure
DMAP, Boc2O
THF
RT, 60 min, 96%
intermediate structure
NBS, AIBN
hv
CCl4
65 °C, 2 h
intermediate structure
NaHCO3
H2O, THF
RT, 60 min
intermediate structure
MnO2
CH2Cl2
RT, 20 h, 69% (3 steps)
intermediate structure
Special reagent
Et3N, TiCl4
THF
RT, 2 h, 78%
intermediate structure
K2CO3, mCPBA
CH2Cl2
0 °C to Reflux, 25 h, 39%
"Also isolated was a sulfoxide (31% yield) which was oxidized to the desired product."
intermediate structure
Special reagent
KOt-Bu
THF
0 °C to RT, 30 min, 62%
intermediate structure
Na.Naphthalene
THF
-78 °C
intermediate structure
AlCl3
CH2Cl2
0 °C to RT, 35 min, 67% (2 steps)
intermediate structure
AcOH, CH2O, NaBH3CN
H2O, MeOH
RT, 15 min, 92%
intermediate structure