Synthesis of Nupharamine

Structure of Nupharamine

C15H25NO2

Principal investigatorIsao Shimizu
Publication year1990
Synthesis typeTotal
Number of steps 9 (linear)
References
Chem. Lett. 1990, 777.
Part 1 of 1
intermediate structure
t-BuOOH, (-)-DET, Ti(Oi-Pr)4
CH2Cl2
-23 °C, 92%
See the Sharpless Epoxidation
intermediate structure
Et3N, DMSO, (COCl)2
CH2Cl2
-78 °C, 91%
See the Swern Oxidation
intermediate structure + intermediate structure
NaH
THF
0 °C, 87%
See the Horner-Wadsworth-Emmons Reaction
intermediate structure
Ph3P, Pd2(dba)3.CHCl3, HCO2H
Dioxane , Et3N
RT, 8 h, 72%
intermediate structure
Pd/C, H2
Et3N, EtOAc
96%
intermediate structure
Ph3P, DEAD, (PhO)2P(O)N3
THF
50%
See the Mitsunobu Reaction
intermediate structure
Ph3P
THF
Reflux, 90%
intermediate structure
NaBH4
EtOH
0 °C, 84%
intermediate structure
HF
MeOH
73%
intermediate structure
Report an error in this part