Synthesis of Melithiazole C

Structure of Melithiazole C

C16H21NO5S

Principal investigatorJanine Cossy
Publication year2007
Synthesis typeTotal
Number of steps 8 (2 parts)
References
Org. Lett. 2007, 9, 3425.
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
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Part 2 of 2
intermediate structure
i-Pr2NEt, Acrolein, n-Bu2BOTf
CH2Cl2
-78 to 0 °C, 90 min, 93%
See the Evans Asymmetric Aldol Addition
intermediate structure
2,6-Di-tert-butylpyridine, MeOTf
CH2Cl2
RT, 40 h, 85%
intermediate structure
LiOH, H2O2
H2O, THF
0 °C, 60 min
intermediate structure
  1. CDI
  2. i-Pr2NLi , MeOAc
THF
-78 to 0 °C, 4 h, 72% (2 steps)
See the Claisen Condensation
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%
See the Olefin Metathesis
intermediate structure
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