Synthesis of Echinopine A

C15H20O2
Principal investigator | Guangxin Liang |
---|---|
Publication year | 2013 |
Synthesis type | Total |
Number of steps | 18 (linear) |
References |
Part 1 of 1
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DMSO,
Et3N,
Pyr.SO3
CH2Cl2
RT, ON, 25% (2 steps)
See the Parikh-Doering Oxidation
"Also isolated was 26% of the C2 epimer which was epimerized to the desired isomer (Et3N/DCM) in 80% yield."

(CH2OH)2,
TsOH
PhMe
Reflux, 96%

H2,
Pd/C
1 atm
MeOH
RT, 10 h, 99%



NHMeOMe.HCl,
i-PrMgBr
THF
-20 °C, 1 h, 94%


- TMS2NK
- PhNTf2
THF
-78 °C, 2.5 h, 98%

CO,
Et3N,
Pd(OAc)2,
Ph3P
DMF, MeOH
RT, 5 h, 79%

H2O,
HCl
MeOH, THF
RT, 2 h, 97%

TsNHNH2
MeOH
RT, 24 h


hv
PhH
6 h, 66%

LiOH
H2O, MeOH
100 °C, 9 h, 96%

Ph3P,
Cl3CCN
CH2Cl2
RT, 1 h

CH2N2,
Et3N
Et2O
0 °C to RT

