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Named reactions

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Search synthesis

Gelsemine

Chemical structure of Gelsemine
C20H22N2O2
Author Larry E. Overman
Publication year 2005
Synthesis type Total synthesis
Number of steps 30 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
Methyl acrylate, AlCl3
CH2Cl2
-78 °C, 7 h, 98%

Selectivity : 90:10 R/S
See the Diels-Alder Reaction
Chemical structure
SeO2
Dioxane
Reflux, 20 h, 90%

Selectivity : 90:10 R/S
Chemical structure
Ph3P+CH3 Br-, n-BuLi
THF
-78 °C to RT, 3.5 h, 95%

See the Wittig Reaction
Chemical structure
KOH
EtOH, H2O
Reflux, 6 h, 91%
Chemical structure
(PhO)2P(O)N3, (4-MeOPh)CH2OH
PhMe, Et3N
Reflux, 12 h, 72%

See the Curtius Rearrangement
Chemical structure
CF3CO2H, PhOMe
CH2Cl2
RT, 90 min
Chemical structure
KCN, CH2O
THF, Buffer (pH = 7)
RT, 24 h, 81% (2 steps)
Chemical structure
n-Bu4N+ F-
THF
-30 °C to RT, 4 h, 95%
Chemical structure
  1. KH, 18-Crown-6
  2. 2,6-Di-tert-butyl-4-methylpyridine, ClCO2Me
THF
-78 °C to RT, 2.5 h, 81%

See the Cope Rearrangement
Chemical structure
Br2, Pentamethylpyridine
CH2Cl2
-78 °C, 30 min
Chemical structure
(CF3CO)2O
CF3CO2H
Reflux, 14 h, 67% (2 steps)

See the Mannich Reaction
Chemical structure
  1. TMS2NK
  2. TESCl
THF
-78 °C to RT, 60 min
Chemical structure
PhIO, BF3.OEt2
CH2Cl2, MeOH
-78 to 0 °C, 3.5 h
Chemical structure
  1. TMS2NK
  2. Comins' reagent
THF
-78 °C, 30 min, 61% (3 steps)
Chemical structure
CO, (DPPF)2PdCl2, n-Bu3N
3.5 atm
DMF, MeOH
80 °C, 18 h, 94%
Chemical structure
AlMe3, o-Iodoaniline
CH2Cl2
-10 °C to RT, 3.5 h, 81%
Chemical structure
  1. NaH
  2. MeOCH2Cl
THF
RT, 12 h, 86%
Chemical structure
Pd2(dba)3.CHCl3, Ag3PO4, Et3N
THF
66 °C, 13 h, 70%

See the Heck Coupling
Chemical structure
HCl
MeOH, H2O
RT, 48 h, 98%
Chemical structure
i-Bu3Al
PhMe
-50 °C to RT, 5 h, 71%

Also isolated was the C3-epimer (12 % yield).
Chemical structure
VinylOEt, Pyr.TsOH
CH2Cl2
RT, 90 min, 85%
Chemical structure
NaCN
DMSO
150 °C, 18 h, 99%
Chemical structure
MeOTf
CH2Cl2
0 °C, 15 min
Chemical structure
NaCN
DMSO
90 °C, 3 h, 85% (2 steps)
Chemical structure
TsOH
MeOH, CH2Cl2
90 °C, 60 min, 99%
Chemical structure
DBU
PhMe
110 °C, 9 h, 80%
Chemical structure
HCl
DME, H2O
55 °C, 3.5 h
Chemical structure
i-Pr2NEt
MeOH
55 °C, 20 h, 90% (2 steps)
Chemical structure
i-Bu2AlH
PhMe
0 °C to RT, 3 h
Chemical structure
Et3SiH, CF3CO2H
CH2Cl2
45 °C, 15 h, 65% (2 steps)
Chemical structure

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