Synthesis of Nupharamine

Structure of Nupharamine

C15H25NO2

Principal investigatorToshio Honda
Publication year1994
Synthesis typeFormal
Number of steps 10 (linear)
References
J. Chem. Soc., Chem. Commun. 1994, 499.
Part 1 of 1
intermediate structure
Sm, (CH2I)2
HMPA, THF
RT, 86%
"The starting material is obtained from (-)-carvone in 4 steps."
intermediate structure
n-Bu4N+ F-
THF
RT
intermediate structure
i-Bu2AlH
THF
-78 °C, 97% (2 steps)
intermediate structure + intermediate structure
n-BuLi
THF
-15 °C
See the Peterson Olefination
intermediate structure
TsOH
DMF
RT, 70% (2 steps)
intermediate structure + intermediate structure
n-BuLi
THF
-78 °C, 92%
intermediate structure
Ph3P, DEAD, (PhO)2P(O)N3
THF
0 °C, 88%
See the Mitsunobu Reaction
intermediate structure
Ph3P
THF
Reflux
intermediate structure
NaBH4
EtOH
RT, 77% (2 steps)
intermediate structure
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Remaining...
37% (1 step)
"See: Collect. Czech. Chem. Commun., 1991, 56. 1309."
intermediate structure