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Named reactions

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Search synthesis

Echitamidine

Chemical structure of Echitamidine
C20H24N2O3
Author Joan Bosch
Publication year 1997
Synthesis type Total synthesis
Number of steps 17 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
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Chemical structure
K2CO3
DMSO
85-90 °C, 4 h, 72%
Chemical structure
K2CO3, AllylBr
Acetone
Reflux, 3 h, 85%
Chemical structure
Sealed tube
PhMe
180-190 °C, 12 h, 80%

See the Claisen Rearrangement
Chemical structure
O3
CH2Cl2
-78 °C, 5 h
Chemical structure
MeNH2.HCl, NaBH3CN
MeOH
RT, 4 h, 36%

Also isolated was the C7a-epimer (26 % yield).
Chemical structure
ClCO2CH(Cl)CH3, Proton Sponge ®
DCE
0 °C to Reflux, 3.5 h, 100%
Chemical structure
TMSI, TMS2NH
CH2Cl2, Pentane
-20 °C, 6 h, 100%
Chemical structure
(PhSe)2, PhSeCl
THF
-35 °C to RT, 4.5 h, 70%
Chemical structure
  1. O3
  2. i-Pr2NH
CH2Cl2
-78 °C to RT, 72%
Chemical structure
MeOH
Reflux, 3 h, 100%
Chemical structure
Methyl vinyl ketone, Et3N
MeOH
RT, 105 min, 74%

See the Michael Addition
Chemical structure
Me3N+Bn HO-
DME
-20 °C, 2.5 h, 44%

See the Michael Addition
Also isolated was the C2-epimer (14 % yield).
Chemical structure
(CH2SH)2, BF3.OEt2
AcOH
RT, 24 h, 80%
Chemical structure
  1. i-Pr2NLi
  2. MeO2CCN
THF, HMPA
-78 °C to RT, 3.5 h, 50%
Chemical structure
HgO, BF3.OEt2
THF, H2O
RT, 35 min, 86%
Chemical structure
H2, Pd/C, HCl
1 atm
MeOH
RT, 2 h, 80%
Chemical structure
NaBH4
MeOH
0 °C to RT, 3 h, 75%
Chemical structure

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