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Named reactions

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Search synthesis

Thiarubrine B

Chemical structure of Thiarubrine_B
C13H8S2
Author Eric Block
Publication year 1994
Synthesis type Total synthesis
Number of steps 12 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
  1. n-BuLi
  2. S8
  3. BnBr
Et2O
-78 °C to RT, ON, 100%
Chemical structure
n-Bu4N+ F-
THF, H2O
RT, 2.5 h, 96%
Chemical structure
O2, CuCl, (CH2NMe2)2
Acetone
RT, 3 h, 97%

See the Glaser-Hay Coupling
Chemical structure
Ph3SnH, Pd(PPh3)4, Et3B
PhMe, Hexane(s)
-30 °C to RT, ON, 56%
Chemical structure
I2
CH2Cl2
0 °C, 2 h, 97%
Chemical structure
Trimethylsilylacetylene, Pd(PPh3)2Cl2, Et2NH, CuI
PhH
RT, 38 h, 86%

See the Sonogashira Coupling
Chemical structure
I2
CH2Cl2
0 °C, 2 h, 95%
Chemical structure + Chemical structure
Pd(PPh3)2Cl2, Et2NH, CuI
PhH
RT, 40 h, 57%

See the Sonogashira Coupling
Chemical structure
n-Bu4N+ F-
THF
RT, 3 h, 86%
Chemical structure
VinylBr, Pd(PPh3)2Cl2, Et2NH, CuI
PhH
RT, 16 h, 70%

See the Sonogashira Coupling
Chemical structure
Reagent structure
Li, AcCl
THF
-85 °C to RT, 8 h

See the Birch Reduction
Chemical structure
KOH, I2
MeOH
-35 to 0 °C, 17% (2 steps)
Chemical structure

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