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Named reactions

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Strychnine

"Dedicated to my colleague and friend David Goldsmith on the occasion of his 75th birthday."

Chemical structure of Strychnine
C21H22N2O2
Author Albert Padwa
Publication year 2007
Synthesis type Total synthesis
Number of steps 17 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
+
Chemical structure
n-BuLi
THF
0 °C, 40 min, 68%
Chemical structure
AcCl, NaOH, n-Bu4N+ HSO4-
CH2Cl2
0 °C to RT, 35 min, 88%
Chemical structure
Mg(ClO4)2
MeCN
45 °C, 90 min, 77%
Chemical structure + Chemical structure
NaH
DMF
0 °C, 5 h, 84%
Chemical structure
MgI2
µW
PhMe
150 °C, 3 h, 95%

See the Diels-Alder Reaction
Chemical structure
NaBH4
EtOH, THF
0 °C, 30 min
Chemical structure
NaOMe
MeOH, THF
RT, 15 min
Chemical structure
LiAlH4
THF
Reflux, 3 h
Chemical structure
NaBH(OAc)3
DCE
-20 °C, 3 h, 65% (4 steps)
Chemical structure
H2, Pd(OH)2/C
4 atm
MeOH
RT, 2 d, 70%
Chemical structure + Chemical structure
K2CO3
DMF, H2O
0 °C, 12 h, 80%
Chemical structure
3,5-Dimethoxybenzaldehyde, NaBH(OAc)3
DCE, AcOH
0 °C to RT, 12 h, 86%
Chemical structure
n-Pr4N+ RuO4-, NMO
4Å MS
MeCN
0 °C to RT, 2.5 h, 80%

See the Ley-Griffith Oxidation
Chemical structure
Pd(PPh3)4, KOPh
THF
Reflux, 2 h, 56%
Chemical structure
Ph2P(O)CH2OMe, i-Pr2NLi
THF
0 °C to RT, 25 h, 72%

See the Horner-Wadsworth-Emmons Reaction
Chemical structure
HCl
THF, H2O
55 °C, 10 h
Chemical structure
Malonic Acid, NaOAc
Ac2O, AcOH
120 °C, 2 h, 43% (2 steps)
Chemical structure

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