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Named reactions

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Melithiazole C

"Dedicated to the memory of Charles Mioskowski (1946-2007)."

Chemical structure of Melithiazole_C
C16H21NO5S
Author Janine Cossy
Publication year 2007
Synthesis type Total synthesis
Number of steps 8 (2 parts)
Reference

Browse hundreds of other total syntheses.

Part 1 of 2
Chemical structure
  1. n-BuLi
  2. N-Acetylmorpholine
THF
-78 °C to RT, 2.5 h, 81%
Chemical structure
Pd(PPh3)4, VinylSnBu3
Dioxane
100 °C, 16 h, 91%

See the Stille Coupling
Chemical structure

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Part 2 of 2
Chemical structure
n-Bu2BOTf, i-Pr2NEt, Acrolein
CH2Cl2
-78 to 0 °C, 90 min, 93%

See the Evans Asymmetric Aldol Addition
Chemical structure
MeOTf, 2,6-Di-tert-butylpyridine
CH2Cl2
RT, 40 h, 85%
Chemical structure
LiOH, H2O2
THF, H2O
0 °C, 60 min
Chemical structure
  1. CDI
  2. MeOAc, i-Pr2NLi
THF
-78 to 0 °C, 4 h, 72% (2 steps)

See the Claisen Condensation
Chemical structure
HC(OMe)3, H2SO4
MeOH
RT, 48 h, 84%
Chemical structure + Chemical structure
Grubbs catalyst (2nd gen.)
CH2Cl2
40 °C, 60 h, 56%

See the Olefin Metathesis
Chemical structure

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