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Named reactions

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Search synthesis

Nupharamine

Chemical structure of Nupharamine
C15H25NO2
Author Toshio Honda
Publication year 1994
Synthesis type Formal synthesis
Number of steps 10 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
Sm, (CH2I)2
THF, HMPA
RT, 86%

The starting material is obtained from (-)-carvone in 4 steps.
Chemical structure
n-Bu4N+ F-
THF
RT
Chemical structure
i-Bu2AlH
THF
-78 °C, 97% (2 steps)
Chemical structure + Chemical structure
n-BuLi
THF
-15 °C

See the Peterson Olefination
Chemical structure
TsOH
DMF
RT, 70% (2 steps)
Chemical structure + Chemical structure
n-BuLi
THF
-78 °C, 92%
Chemical structure
(PhO)2P(O)N3, DEAD, Ph3P
THF
0 °C, 88%

See the Mitsunobu Reaction
Chemical structure
Ph3P
THF
Reflux
Chemical structure
NaBH4
EtOH
RT, 77% (2 steps)
Chemical structure

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Remaining...
37% (1 step)

See: Collect. Czech. Chem. Commun., 1991, 56. 1309.
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