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Named reactions

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Search synthesis

Longifolene

Chemical structure of Longifolene
C15H24
Author John E. McMurry
Publication year 1972
Synthesis type Total synthesis
Number of steps 18 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
(CH2OH)2, TsOH
Dean-Stark
PhH
Reflux, 25 min
Chemical structure
H2, Pd/C
1 atm
EtOH
RT, 45 min, 85 % (2 steps)
Chemical structure
MeMgI
Et2O
RT, 4.5 h

See the Grignard Reaction
Chemical structure
H2SO4
Cyclohexane, H2O
RT, 45 min, 96 % (2 steps)
Chemical structure
mCPBA
CHCl3
0 °C to RT, ON, 100 %

See the Prilezhaev Reaction
Chemical structure
NaH
DMSO
60 °C, 5.5 d, 93 %
Chemical structure
H2SO4
Cyclohexane, CH2Cl2, H2O
RT, 15 min, 85 %
Chemical structure
KOt-Bu, CHBr3
Pentane
0 °C to RT, 2.5 h, 85 %
Chemical structure
AgClO4
Acetone, H2O
45 °C, 17 h, 100 %
Chemical structure
Na
NH3, MeOH
-33 °C, 62 %
Chemical structure
CrO3.2Pyr
CH2Cl2
RT, 15 min, 100 %

See the Collins Oxidation
Chemical structure
Me2CuLi
Et2O
-20 °C, 40 min, 96 %

See the Michael Addition
See the Aldol Addition
Chemical structure
NaBH4, NaOH
MeOH
0 °C to RT, ON, 97 %
Chemical structure
MsCl, Et3N
CH2Cl2
-20 to -10 °C, 15 min, 100 %
Chemical structure
KOt-Bu
t-BuOH
35 °C, 60 min, 100 %

See the Grob Fragmentation
Chemical structure
H2, (Ph3P)3RhCl
1 atm
PhH, MeOH
RT, 4.5 d, 87 %
Chemical structure
MeLi
Et2O
48 °C, 3 h
Chemical structure
SOCl2
Pyr
0 °C, 10 min, 85 % (2 steps)
Chemical structure

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