Synthesis of Melithiazole C

Structure of Melithiazole C

C16H21NO5S

Principal investigatorJanine Cossy
Publication year2007
Synthesis typeTotal
Number of steps 8 (2 parts)
References
Part 1 of 2
intermediate structure
  1. n-BuLi
  2. N-Acetylmorpholine
THF
-78 °C to RT, 2.5 h, 81%
intermediate structure
Pd(PPh3)4, VinylSnBu3
Dioxane
100 °C, 16 h, 91%
See the Stille Coupling
intermediate structure
Part 2 of 2
intermediate structure
n-Bu2BOTf, i-Pr2NEt, Acrolein
CH2Cl2
-78 to 0 °C, 90 min, 93%
intermediate structure
MeOTf, 2,6-Di-tert-butylpyridine
CH2Cl2
RT, 40 h, 85%
intermediate structure
LiOH, H2O2
THF, H2O
0 °C, 60 min
intermediate structure
  1. CDI
  2. MeOAc
  3. i-Pr2NLi
THF
-78 to 0 °C, 4 h, 72% (2 steps)
intermediate structure
HC(OMe)3, H2SO4
MeOH
RT, 48 h, 84%
intermediate structure + intermediate structure
Grubbs catalyst (2nd gen.)
CH2Cl2
40 °C, 60 h, 56%
intermediate structure