Synthesis of Thiarubrine A

Structure of Thiarubrine A

C13H8S2

Principal investigatorMasato Koreeda
Publication year1994
Synthesis typeTotal
Number of steps 8 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
KOH
DMF
RT, 3.5 h, 87%
intermediate structure
Dess-Martin Periodinane
CH2Cl2
RT, 30 min, 91%
intermediate structure
CBr4, Ph3P
CH2Cl2
0 °C, 50 min, 89%
intermediate structure
  1. n-BuLi
  2. MeI
  3. BF3.OEt2
  4. DMF
THF
-78 °C to RT, 9.5 h
intermediate structure
CBr4, Ph3P
CH2Cl2
0 °C, 50 min, 34% (2 steps)
intermediate structure
n-BuLi
THF
-78 °C to RT, 9.5 h, 54%
intermediate structure
VinylBr, Pd(PPh3)4, CuI, Et3N
PhMe
RT, 4.5 h, 41%
intermediate structure
n-Bu4N+ F-, I2
THF
RT, 3 h, 53%
intermediate structure