Synthesis of Pentacycloanammoxic Acid

Structure of Pentacycloanammoxic Acid

C20H30O2

Principal investigator	Elias J. Corey
Publication year	2004
Synthesis type	Total
Number of steps	15 (linear)
References	J. Am. Chem. Soc. 2004, 126, 15664.

Part 1 of 1

intermediate structure

Br2

intermediate structure

DBAD

See the Diels-Alder Reaction

intermediate structure

H2, NaNO2, PtO2

1 atm

EtOH, THF

RT

intermediate structure

Zn

AcOH

95 °C, 60 min, 80% (2 steps)

intermediate structure

2-Cyclopentenone

hν

MeCN

RT, 12 h, 40%

intermediate structure

H2 , Pd/C
O2

1 atm

EtOH

RT, 2.5 h, 76%

intermediate structure

HC(OMe)3, TsOH

MeOH

40 °C, 60 min, 91%

intermediate structure

AcOH

hν

H2O, MeCN

50 °C, 3 h, 6%

intermediate structure

HCO2Et, NaOMe

PhH

RT, 12 h

See the Claisen Condensation

intermediate structure

Et3N, TsN3

CH2Cl2

RT, 20 h, 80% (2 steps)

intermediate structure

Et3N

hν

MeOH

RT, 3 h, 72%

See the Wolff Rearrangement

intermediate structure

i-Bu2AlH

PhMe

-78 °C, 30 min

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C to RT, 6 d, 91% (2 steps)

See the Swern Oxidation

intermediate structure

i-Pr2NLi, Ph3P(CH2)6CO2H+ Br-

THF

-78 °C to RT, 7.5 h, 67%

See the Wittig Reaction

intermediate structure

NH2NH2, O2, CuSO4

1 atm

EtOH, H2O

RT, 12 h, 88%

intermediate structure

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