Synthesis of Azadiradione

Structure of Azadiradione

C28H34O5

Principal investigator	Elias J. Corey
Publication year	1989
Synthesis type	Total
Number of steps	27 (linear)
References	Tetrahedron Lett. 1989, 30, 3023.

Part 1 of 1

intermediate structure

Et3N, MsCl

CH2Cl2

-20 °C, 30 min

intermediate structure

LiBr

THF

-20 °C, 2 h, 96% (2 steps)

See the Finkelstein Reaction

intermediate structure

Special reagent

(EtO)2P(O)Cl

THF

-78 to -20 °C, 5 h, 80%

intermediate structure

Hg(CF3CO2)2
NaCl , H2O

MeNO2

0 °C, 2.5 h, 27%

intermediate structure

NaBH4, O2

DMF

RT, 91%

intermediate structure

H2SO4, CrO3

Acetone, H2O

0 °C, 86%

See the Jones Oxidation

intermediate structure

NaH, (EtO)2P(O)Cl

THF

0 °C to Reflux, 70 min

intermediate structure

(CH2OH)2, TsOH

Dean-Stark

PhH

Reflux, 87% (2 steps)

intermediate structure

i-Bu2AlH

PhMe

-20 °C, 30 min, 90%

intermediate structure

HOSO2ONO

Pyr

0 °C, 30 min

intermediate structure

hv

CH2Cl2

50 °C, 28% (2 steps)

See the Barton Reaction

intermediate structure

MeCHO, HCl

H2O

RT, 12 h

"No yield reported."

intermediate structure

NaBH(OAc)3

Acetone, AcOH

-78 °C, 20 min

"No yield reported."

intermediate structure

Special reagent

NaOEt
HCl , H2O

EtOH

10 °C to Reflux, 20 min, 90%

See the Michael Addition

See the Nef Reaction

intermediate structure

NaOEt

EtOH

70 °C, 45 min

See the Aldol Condensation

intermediate structure

MeOCH2Br, i-Pr2NEt, n-Bu4N+ I-

MeCN

70 °C, 7 h, 92%

intermediate structure

Li(s-Bu)3BH

THF

-78 °C, 30 min

intermediate structure

DEAD, Ph3P, BzOH

THF

RT, 3 h

See the Mitsunobu Reaction

intermediate structure

NaOH

EtOH

RT, 12 h, 50% (3 steps)

intermediate structure

Zn-Ag

CH2Cl2, Et2O

0 °C, 61%

See the Simmons-Smith Reaction

intermediate structure

Dess-Martin Periodinane

CH2Cl2

RT, 10 min, 100%

See the Dess-Martin Oxidation

intermediate structure

Li

NH3, THF

intermediate structure

Dess-Martin Periodinane

CH2Cl2

92% (2 steps)

See the Dess-Martin Oxidation

intermediate structure

i-Pr2NLi
PhSeBr

THF

"No yield reported."

intermediate structure

H2O2

H2O, Pyr

"No yield reported."

intermediate structure

TMSBr

CH2Cl2

-20 °C, 17 h, 91%

intermediate structure

Ac2O, DMAP

THF

RT, 17 h

"No yield reported."

intermediate structure

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