Synthesis of Wodeshiol

Structure of Wodeshiol

C20H18O8

Principal investigatorElias J. Corey
Publication year1999
Synthesis typeTotal
Number of steps 8 (linear)
References
Part 1 of 1
intermediate structure
VinylLi
THF
-78 °C, 30 min, 97%
intermediate structure
MnO2
CH2Cl2
0 °C, 30 min, 75%
intermediate structure
Br2, Et3N
CH2Cl2, Et2O
-78 to 0 °C, 16.5 h, 70%
intermediate structure
CBS Reagent
CH2Cl2, PhMe
-78 °C, 5.5 d, 84%
intermediate structure
  1. t-BuLi
  2. n-Bu3SnCl
Et2O
-78 to -40 °C, 5 h, 84%
intermediate structure
CuCl, Pd(PPh3)4, CuCl2
DMSO
60 °C, 2 h, 82%
See the Stille Coupling
intermediate structure
t-BuOOH, VO(acac)2
CH2Cl2
0 °C, 14 h, 56%
intermediate structure
Pyr.TsOH
PhH
80 °C, 22 h, 61%
intermediate structure