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Named reactions

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Search synthesis

Nupharamine

Chemical structure of Nupharamine
C15H25NO2
Author José Barluenga
Publication year 1999
Synthesis type Total synthesis
Number of steps 12 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
+
Chemical structure
ZnCl2
THF
-80 °C to RT, 16 h, 51%

Selectivity : >99:01 er
See the Diels-Alder Reaction
Chemical structure
Triphosgene, Et3N
THF
0 °C, 15 min, 95%
Chemical structure
  1. TMS2NLi
  2. Comins' reagent
THF
-80 °C, 3 h, 67%

The yield was 96 % brsm.
Chemical structure
H2, PtO2
1 atm
EtOH
RT, 6-8 h, 89%
Chemical structure
KOt-Bu
THF
0 °C, 30 min, 95%
Chemical structure
TBSCl, Imidazole
MeCN
RT, 4 h, 67%
Chemical structure
ClCO2Bn, K2CO3
MeCN
RT, 4 h, 99%
Chemical structure
HCl
THF, H2O
RT, 30 min, 88%
Chemical structure + Chemical structure
  1. (COCl)2, DMSO, Et3N
  2. Ph3P=CHCO2Et
CH2Cl2
-65 °C to RT, 5 h

See the Swern Oxidation
See the Wittig Reaction
Chemical structure
H2, Pd/C
1 atm
EtOH
RT, 3.5 h, 85%
Chemical structure
MeLi
THF
-70 °C, 15 min, 77%
Chemical structure
Pd, HCO2NH4
MeOH
RT, 14 h, 99%
Chemical structure

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