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Named reactions

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Quadrone

Chemical structure of Quadrone
C15H20O3
Author Samuel J. Danishefsky
Publication year 1981
Synthesis type Total synthesis
Number of steps 19 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
+
Chemical structure
VinylMgBr, (n-Bu3PCuI)4
THF, HMPA
-45 °C to RT, 3 h, 54%

See the Michael Addition
Chemical structure
TsOH, (CH2OH)2
Dean-Stark
PhMe
Reflux, 3 h
Chemical structure
  1. BH3.THF
  2. H2O2, NaOH, H2O
THF
0 to 50 °C, 3 h
Chemical structure
MsCl, Et3N
Et2O
0 °C to RT, 3 h
Chemical structure
LiBr
Acetone
Reflux, 6 h

See the Finkelstein Reaction
Chemical structure
NaOMe
MeOH
0 °C, 2 h, 47% (5 steps)

See the Knoevenagel Condensation
Chemical structure + Chemical structure
TiCl4
CH2Cl2
-78 °C to RT, 40 min

See the Michael Addition
R = H, t-Bu.
Chemical structure
HCl
Dioxane , H2O
Reflux, 90 min

R = H, t-Bu.
Chemical structure
CH2N2
CH2Cl2
74% (3 steps)
Chemical structure
TsOH, (CH2OH)2
Dean-Stark
PhMe
Reflux, 4 h, 93%
Chemical structure
NaI, Pyr
Acetone
Reflux, 15 h

See the Finkelstein Reaction
Chemical structure
i-Pr2NLi
THF, HMPA
-78 to -23 °C, 2 h
Chemical structure
TsOH
Acetone
RT, 60 min, 56% (3 steps)
Chemical structure
KOH
MeOH
Reflux, 90 min, 100%
Chemical structure
PhSeCl
EtOAc
RT, 3 h
Chemical structure
H2O2, Pyr
CH2Cl2
78% (2 steps)
Chemical structure
  1. i-Pr2NLi
  2. CH2O
THF
-23 °C, 80 min, 60%

See the Aldol Addition
Chemical structure
H2, Pd/C
1 atm
MeOH
RT, 60 min
Chemical structure
190-195 °C, 6 min, 51% (2 steps)
Chemical structure

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