Synthesis of Thiarubrine B

Structure of Thiarubrine B

C13H8S2

Principal investigatorEric Block
Publication year1994
Synthesis typeTotal
Number of steps 12 (linear)
References
J. Am. Chem. Soc. 1994, 116, 9403.
Part 1 of 1
intermediate structure
  1. n-BuLi
  2. S8
  3. BnBr
Et2O
-78 °C to RT, ON, 100%
intermediate structure
n-Bu4N+ F-
H2O, THF
RT, 2.5 h, 96%
intermediate structure
CuCl, O2, (CH2NMe2)2
Acetone
RT, 3 h, 97%
See the Glaser-Hay Coupling
intermediate structure
Et3B, Pd(PPh3)4, Ph3SnH
Hexane(s), PhMe
-30 °C to RT, ON, 56%
intermediate structure
I2
CH2Cl2
0 °C, 2 h, 97%
intermediate structure
Trimethylsilylacetylene, Pd(PPh3)2Cl2, CuI, Et2NH
PhH
RT, 38 h, 86%
See the Sonogashira Coupling
intermediate structure
I2
CH2Cl2
0 °C, 2 h, 95%
intermediate structure + intermediate structure
CuI, Et2NH, Pd(PPh3)2Cl2
PhH
RT, 40 h, 57%
See the Sonogashira Coupling
intermediate structure
n-Bu4N+ F-
THF
RT, 3 h, 86%
intermediate structure
CuI, Et2NH, Pd(PPh3)2Cl2, VinylBr
PhH
RT, 16 h, 70%
See the Sonogashira Coupling
intermediate structure
Special reagent
AcCl, Li
THF
-85 °C to RT, 8 h
See the Birch Reduction
intermediate structure
KOH, I2
MeOH
-35 to 0 °C, 17% (2 steps)
intermediate structure
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