Synthesis of Quadrone

C15H20O3
Principal investigator | Samuel J. Danishefsky |
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Publication year | 1981 |
Synthesis type | Total |
Number of steps | 19 (linear) |
References |
Part 1 of 1
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(CH2OH)2,
TsOH
Dean-Stark
PhMe
Reflux, 3 h

- BH3.THF
- NaOH , H2O2 , H2O
THF
0 to 50 °C, 3 h

Et3N,
MsCl
Et2O
0 °C to RT, 3 h





HCl
Dioxane , H2O
Reflux, 90 min
"R = H, t-Bu."

CH2N2
CH2Cl2
74% (3 steps)

(CH2OH)2,
TsOH
Dean-Stark
PhMe
Reflux, 4 h, 93%


i-Pr2NLi
HMPA, THF
-78 to -23 °C, 2 h

TsOH
Acetone
RT, 60 min, 56% (3 steps)

KOH
MeOH
Reflux, 90 min, 100%

PhSeCl
EtOAc
RT, 3 h

H2O2,
Pyr
CH2Cl2
78% (2 steps)


H2,
Pd/C
1 atm
MeOH
RT, 60 min

190-195 °C, 6 min, 51% (2 steps)
