Synthesis of Streptonigrone

Structure of Streptonigrone

C24H22N4O7

Principal investigator	Dale L. Boger
Publication year	1993
Synthesis type	Total
Number of steps	18 (linear)
References	J. Am. Chem. Soc. 1993, 115, 10733.

Part 1 of 1

intermediate structure

+

intermediate structure

NaOH

MeOH

57 °C, 6 h

See the Friedländer synthesis

intermediate structure

HCl

MeOH

RT, 5 h, 85%

See the Fischer-Speier Esterification

intermediate structure

i-Pr2NLi, EtOAc

Hexane(s), THF

-78 °C to RT, 55 min, 71%

See the Claisen Condensation

intermediate structure

+

intermediate structure

Piperidine

EtOH

Reflux, 60 min, 81%

See the Knoevenagel Condensation

intermediate structure

Et3N, MsNH2, TiCl4

CH2Cl2

0 °C to RT, 6.5 h, 75%

intermediate structure

+

intermediate structure

PhH

RT, 3 h

See the Diels-Alder Reaction

intermediate structure

KOt-Bu

THF

-30 °C, 60 min

intermediate structure

DDQ

CH2Cl2

RT, 60 min, 65% (3 steps)

intermediate structure

LiOH

DMSO, H2O

60 °C, 7 h, 97%

intermediate structure

NaH, MeOCH2Cl

DMF

0 °C to RT, 2 h, 96%

intermediate structure

LiOH

DMSO, H2O

130 °C, 6 h, 80%

intermediate structure

(PhO)2P(O)N3, Et3N

PhH

RT to Reflux, 7.5 h, 84%

See the Curtius Rearrangement

intermediate structure

HBr

CH2Cl2

0 °C, 2 h, 80%

intermediate structure

Special reagent

n-Bu4N+ HSO4-

CH2Cl2, H2O

RT, 4 h, 69%

intermediate structure

NaOMe, Ti(Oi-Pr)4

THF

0 °C, 105 min, 44%

intermediate structure

NaN3

H2O, THF

RT, 21 h, 85%

intermediate structure

NaBH4

MeOH, THF

RT, 60 min, 86%

intermediate structure

H2, HBr, Pd/C

CF3CH2OH

80 °C, 60 min

"No yield reported."

intermediate structure

Report an error in this part