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Named reactions

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Quadrone

Chemical structure of Quadrone
C15H20O3
Author Steven D. Burke
Publication year 1982
Synthesis type Formal synthesis
Number of steps 26 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
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Chemical structure
THF
-78 °C to RT, 4.5 h, 77%
Chemical structure
LiAlH4
Et2O
0 °C, 4 h, 99%
Chemical structure
VinylOEt, Hg(OAc)2
Reflux, ON
Chemical structure
Sealed tube
187 to 200 °C, 6 h, 94% (2 steps)

See the Claisen Rearrangement
Chemical structure
CrO3, H2SO4
Acetone, H2O
0 °C to RT, 8.5 h, 98%

See the Jones Oxidation
Chemical structure
(COCl)2
PhH
RT, 8.5 h
Chemical structure
TiCl4
CH2Cl2
-30 °C to RT, 16 h, 84% (2 steps)
Chemical structure
OsO4, NMO
Acetone, H2O

See the Upjohn Dihydroxylation
Chemical structure
NaIO4
THF, H2O
94% (2 steps)
Chemical structure
Morpholine, TsOH
PhH
Reflux, 92%

See the Michael Addition
Chemical structure
NaOH, Dibenzo-18-crown-6
PhH
Reflux, 96%

See the Claisen-Schmidt Condensation
Chemical structure
TsOH, (CH2OH)2
PhH
Reflux
Chemical structure
t-BuOOH, NaOH
MeOH, H2O
RT, 89% (2 steps)

See the Michael Addition
Chemical structure
NH2NH2
AcOH, MeOH
92%

See the Wharton Reaction
Chemical structure
VinylOEt, Hg(OAc)2
Sealed tube
Xylene(s)
250 °C, 90%

See the Claisen Rearrangement
Chemical structure
H2, Pd/C
1 atm
EtOH
RT, 100%
Chemical structure
KOAc
Ac2O
Reflux
Chemical structure
OsO4, NaIO4
THF, H2O
57% (2 steps)

See the Lemieux-Johnson Oxidation
Chemical structure
CrO3, H2SO4
H2O

See the Jones Oxidation
Chemical structure
CH2N2
Et2O
60% (2 steps)
Chemical structure

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Remaining...
24% (6 steps)

See : J. Am. Chem. Soc. 1981, 103, 4136.
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