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

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

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

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

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

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

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