Synthesis of Promothiocin A

Structure of Promothiocin A

C36H37N11O8S2

Principal investigatorChristopher J. Moody
Publication year2000
Synthesis typeTotal
Number of steps 31 (3 parts)
References
Part 1 of 3
intermediate structure + intermediate structure
Rh2(OAc)4
CHCl3
Reflux, 6.5 h, 71 %
intermediate structure
I2, Ph3P, Et3N
CH2Cl2
RT, , 56%
intermediate structure
H2, Pd/C
MeOH
RT, 4 h, 100%
intermediate structure + intermediate structure
N-Methylmorpholine
THF
-10 to 0 °C, 60 min, 87%
intermediate structure
LiOH
THF, H2O
RT, ON, 93%
intermediate structure + intermediate structure
ClCO2i-Bu, N-Methylmorpholine
THF
0 °C to RT, 90 min, 84%
intermediate structure
AcCl
EtOH
RT, ON, 100%
intermediate structure
Part 2 of 3
intermediate structure + intermediate structure
Rh2(OAc)4
CHCl3
Reflux, ON, 80%
intermediate structure
I2, Ph3P, Et3N
CH2Cl2
RT, ON, 70%
intermediate structure
LiOH
MeOH, H2O
RT, 5 h, 95%
intermediate structure + intermediate structure
ClCO2Et, Et3N
THF
0 °C to RT, ON, 77%
intermediate structure
NH4OAc
PhH, AcOH
Reflux, 24 h, 85%
intermediate structure + intermediate structure
EtOH
50 °C, ON, 83%
intermediate structure
LiOH
THF, H2O
RT to 45 °C, 2.5 d, 92%
intermediate structure
  1. ClCO2Et
  2. Et3N
  3. NH3
  4. H2O
THF
-10 °C to RT, 2 h, 85%
intermediate structure
PhH
Reflux, 5 h, 59%
intermediate structure + intermediate structure
KHCO3
THF
-3 °C, 16 h
intermediate structure
(CF3CO)2O, 2,6-Lutidine
THF
0 °C, 3 h, 72% (2 steps)
intermediate structure
LiOH
THF, H2O
RT, ON, 94%
intermediate structure
Part 3 of 3
intermediate structure + intermediate structure
ClCO2i-Bu, N-Methylmorpholine
THF
0 °C, 90 min, 69%
intermediate structure
LiOH
THF, H2O
RT, ON, 94%
intermediate structure
EDC, C6F5OH
CH2Cl2
0 °C to RT, ON
intermediate structure
HCl
Dioxane
RT, 3.5 h
intermediate structure
Et3N
CHCl3
RT, 4 d, 55% (3 steps)
intermediate structure
BCl3, Me2S
CH2Cl2
0 °C to RT, ON, 39%
intermediate structure
IBX
DMSO
RT, 4.5 h, 81%
intermediate structure
NaClO2, NaH2PO4, 2-Methyl-2-butene
t-BuOH, H2O
RT, 5 h, 70%
intermediate structure + intermediate structure
EDC
CH2Cl2
RT, ON, 50%
intermediate structure
n-Bu4N+ F-
THF
RT, 90 min, 57%
intermediate structure
MsCl, Et3N
CH2Cl2
RT, 60 min
intermediate structure
Et3N
CH2Cl2
RT, ON, 59% (2 steps)
intermediate structure