Synthesis of Azadiradione

C28H34O5
Principal investigator | Elias J. Corey |
---|---|
Publication year | 1989 |
Synthesis type | Total |
Number of steps | 27 (linear) |
References |
Part 1 of 1

Et3N,
MsCl
CH2Cl2
-20 °C, 30 min



(EtO)2P(O)Cl
THF
-78 to -20 °C, 5 h, 80%

- Hg(CF3CO2)2
- NaCl , H2O
MeNO2
0 °C, 2.5 h, 27%

NaBH4,
O2
DMF
RT, 91%


NaH,
(EtO)2P(O)Cl
THF
0 °C to Reflux, 70 min

(CH2OH)2,
TsOH
Dean-Stark
PhH
Reflux, 87% (2 steps)

i-Bu2AlH
PhMe
-20 °C, 30 min, 90%

HOSO2ONO
Pyr
0 °C, 30 min


MeCHO,
HCl
H2O
RT, 12 h
"No yield reported."

NaBH(OAc)3
Acetone, AcOH
-78 °C, 20 min
"No yield reported."



MeOCH2Br,
i-Pr2NEt,
n-Bu4N+ I-
MeCN
70 °C, 7 h, 92%

Li(s-Bu)3BH
THF
-78 °C, 30 min


NaOH
EtOH
RT, 12 h, 50% (3 steps)



Li
NH3, THF


- i-Pr2NLi
- PhSeBr
THF
"No yield reported."

H2O2
H2O, Pyr
"No yield reported."

TMSBr
CH2Cl2
-20 °C, 17 h, 91%

Ac2O,
DMAP
THF
RT, 17 h
"No yield reported."
