Synthesis of Nupharamine

Structure of Nupharamine

C15H25NO2

Principal investigatorRoderick W. Bates
Publication year2010
Synthesis typeTotal
Number of steps 16 (linear)
References
Synlett 2010, 866.
Part 1 of 1
intermediate structure + intermediate structure
AcOH
See the Johnson-Claisen Rearrangement
intermediate structure
LiAlH4
Et2O
65% (2 steps)
intermediate structure + intermediate structure
DIAD, Ph3P
78%
See the Mitsunobu Reaction
intermediate structure
NH2NH2
100%
intermediate structure
NaOH, Boc2O
95%
intermediate structure
AgOTf
4 Å MS
CH2Cl2
91%
intermediate structure
NaBH4, Mo(CO)6
H2O, MeCN
83%
intermediate structure
Et3N, (COCl)2, DMSO
CH2Cl2
See the Swern Oxidation
intermediate structure + intermediate structure
Ba(OH)2
H2O, THF
87% (2 steps)
See the Horner-Wadsworth-Emmons Reaction
intermediate structure
Methyl acrylate, Grubbs-Hoveyda catalyst (2nd gen.)
PhMe
70 °C, 75%
See the Olefin Metathesis
intermediate structure
H2, (Ph3P)3RhCl
7 atm
PhMe
94%
intermediate structure
CF3CO2H
CH2Cl2
intermediate structure
NaBH4
MeOH
0 °C, 85% (2 steps)
intermediate structure
K2CO3, ClCO2Bn
intermediate structure
MeMgBr
See the Grignard Reaction
intermediate structure
Pd/C, HCO2NH4
49% (3 steps)
intermediate structure
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