Synthesis of Clostrubin

Structure of Clostrubin

C25H18O6

Principal investigatorAng Li
Publication year2015
Synthesis typeTotal
Number of steps 13 (3 parts)
References
Part 1 of 3
intermediate structure + intermediate structure
SiO2
THF
-78 °C to RT, 8 h
intermediate structure
K2CO3, MeI
DMF
RT, 18 h, 45% (2 steps)
intermediate structure
HCl, SnCl2.2H2O
AcOH, H2O
RT, 30 min
intermediate structure
DBU, TsN3
CH2Cl2
RT, 20 h, 89% (2 steps)
intermediate structure
Part 2 of 3
intermediate structure
(CH2O)n, Et3N, MgCl2
THF
Reflux, , 84%
intermediate structure
MeI, K2CO3
DMF
RT, 24 h, 99%
intermediate structure
  1. MeMgBr
  2. HMPA , TMSCl , Et3N
THF
0 °C to RT, 20 min, 94%
intermediate structure
  1. EtMgBr
  2. CS2
  3. MeI
  4. H2O , HCl
THF
RT to 70 °C, 12 h, 67%
intermediate structure
Dess-Martin Periodinane
CH2Cl2
RT, 1 min, 83%
intermediate structure
NaOMe
MeOH
RT to 50 °C, 4 h, 66%
intermediate structure
Part 3 of 3
intermediate structure + intermediate structure
  1. Rh2(OAc)4
  2. Cu
PhMe
50 to 110 °C, 2 h, 85%
intermediate structure
hv
CHCl3
RT, 8 h, 55%
intermediate structure
HBr
AcOH, H2O
120 °C, 10 h, 95%
intermediate structure