Synthesis of Echitamidine

C20H24N2O3
Principal investigator | Joan Bosch |
---|---|
Publication year | 1997 |
Synthesis type | Total |
Number of steps | 17 (linear) |
References |
Part 1 of 1
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K2CO3
DMSO
85-90 °C, 4 h, 72%

AllylBr,
K2CO3
Acetone
Reflux, 3 h, 85%


O3
CH2Cl2
-78 °C, 5 h

NaBH3CN,
MeNH2.HCl
MeOH
RT, 4 h, 36%
"Also isolated was the C7a-epimer (26 % yield)."

ClCO2CH(Cl)CH3,
Proton Sponge
DCE
0 °C to Reflux, 3.5 h, 100%

TMS2NH,
TMSI
CH2Cl2, Pentane
-20 °C, 6 h, 100%

(PhSe)2,
PhSeCl
THF
-35 °C to RT, 4.5 h, 70%

- O3
- i-Pr2NH
CH2Cl2
-78 °C to RT, 72%

MeOH
Reflux, 3 h, 100%


Me3N+Bn HO-
DME
-20 °C, 2.5 h, 44%
See the Michael Addition
"Also isolated was the C2-epimer (14 % yield)."

BF3.OEt2,
(CH2SH)2
AcOH
RT, 24 h, 80%

- i-Pr2NLi
- MeO2CCN
HMPA, THF
-78 °C to RT, 3.5 h, 50%

BF3.OEt2,
HgO
H2O, THF
RT, 35 min, 86%

H2,
HCl,
Pd/C
1 atm
MeOH
RT, 2 h, 80%

NaBH4
MeOH
0 °C to RT, 3 h, 75%
