Synthesis of Echitamidine

Structure of Echitamidine

C20H24N2O3

Principal investigatorJoan Bosch
Publication year1997
Synthesis typeTotal
Number of steps 17 (linear)
References
J. Am. Chem. Soc. 1997, 119, 7230. Tetrahedron 1996, 52, 4013.
Part 1 of 1
intermediate structure + intermediate structure
K2CO3
DMSO
85-90 °C, 4 h, 72%
intermediate structure
AllylBr, K2CO3
Acetone
Reflux, 3 h, 85%
intermediate structure
Sealed tube
PhMe
180-190 °C, 12 h, 80%
See the Claisen Rearrangement
intermediate structure
O3
CH2Cl2
-78 °C, 5 h
intermediate structure
NaBH3CN, MeNH2.HCl
MeOH
RT, 4 h, 36%
"Also isolated was the C7a-epimer (26 % yield)."
intermediate structure
ClCO2CH(Cl)CH3, Proton Sponge
DCE
0 °C to Reflux, 3.5 h, 100%
intermediate structure
TMS2NH, TMSI
CH2Cl2, Pentane
-20 °C, 6 h, 100%
intermediate structure
(PhSe)2, PhSeCl
THF
-35 °C to RT, 4.5 h, 70%
intermediate structure
  1. O3
  2. i-Pr2NH
CH2Cl2
-78 °C to RT, 72%
intermediate structure
MeOH
Reflux, 3 h, 100%
intermediate structure
Et3N, Methyl vinyl ketone
MeOH
RT, 105 min, 74%
See the Michael Addition
intermediate structure
Me3N+Bn HO-
DME
-20 °C, 2.5 h, 44%
See the Michael Addition
"Also isolated was the C2-epimer (14 % yield)."
intermediate structure
BF3.OEt2, (CH2SH)2
AcOH
RT, 24 h, 80%
intermediate structure
  1. i-Pr2NLi
  2. MeO2CCN
HMPA, THF
-78 °C to RT, 3.5 h, 50%
intermediate structure
BF3.OEt2, HgO
H2O, THF
RT, 35 min, 86%
intermediate structure
H2, HCl, Pd/C
1 atm
MeOH
RT, 2 h, 80%
intermediate structure
NaBH4
MeOH
0 °C to RT, 3 h, 75%
intermediate structure
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