Synthesis of Quadrone

Structure of Quadrone

C15H20O3

Principal investigatorSamuel J. Danishefsky
Publication year1981
Synthesis typeTotal
Number of steps 19 (linear)
References
J. Am. Chem. Soc. 1981, 103, 4136.
Part 1 of 1
intermediate structure + intermediate structure
VinylMgBr, (n-Bu3PCuI)4
HMPA, THF
-45 °C to RT, 3 h, 54%
See the Michael Addition
intermediate structure
(CH2OH)2, TsOH
Dean-Stark
PhMe
Reflux, 3 h
intermediate structure
  1. BH3.THF
  2. NaOH , H2O2 , H2O
THF
0 to 50 °C, 3 h
intermediate structure
Et3N, MsCl
Et2O
0 °C to RT, 3 h
intermediate structure
LiBr
Acetone
Reflux, 6 h
See the Finkelstein Reaction
intermediate structure
NaOMe
MeOH
0 °C, 2 h, 47% (5 steps)
See the Knoevenagel Condensation
intermediate structure + intermediate structure
TiCl4
CH2Cl2
-78 °C to RT, 40 min
See the Michael Addition
"R = H, t-Bu."
intermediate structure
HCl
Dioxane , H2O
Reflux, 90 min
"R = H, t-Bu."
intermediate structure
CH2N2
CH2Cl2
74% (3 steps)
intermediate structure
(CH2OH)2, TsOH
Dean-Stark
PhMe
Reflux, 4 h, 93%
intermediate structure
Pyr, NaI
Acetone
Reflux, 15 h
See the Finkelstein Reaction
intermediate structure
i-Pr2NLi
HMPA, THF
-78 to -23 °C, 2 h
intermediate structure
TsOH
Acetone
RT, 60 min, 56% (3 steps)
intermediate structure
KOH
MeOH
Reflux, 90 min, 100%
intermediate structure
PhSeCl
EtOAc
RT, 3 h
intermediate structure
H2O2, Pyr
CH2Cl2
78% (2 steps)
intermediate structure
  1. i-Pr2NLi
  2. CH2O
THF
-23 °C, 80 min, 60%
See the Aldol Addition
intermediate structure
H2, Pd/C
1 atm
MeOH
RT, 60 min
intermediate structure
190-195 °C, 6 min, 51% (2 steps)
intermediate structure
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