Synthesis of Coccinelline

Structure of Coccinelline

C13H23NO

Principal investigator	Robert V. Stevens
Publication year	1979
Synthesis type	Total
Number of steps	11 (linear)
References	J. Am. Chem. Soc. 1979, 101, 7032.

Part 1 of 1

intermediate structure

+

intermediate structure

NaOMe

MeOH

RT, 12 h, 58%

See the Michael Addition

intermediate structure

TsOH, HC(OMe)3

MeOH

RT, 12 h, 98%

intermediate structure

NaCl

DMF, H2O

Reflux, 35 h, 69%

See the Krapcho Decarboxylation

intermediate structure

NaH

DME

Reflux, 17 h

See the Claisen Condensation

intermediate structure

NaCl

DMF, H2O

Reflux, 35 h, 67% (2 steps)

See the Krapcho Decarboxylation

intermediate structure

NH4OAc, NaBH3CN

3 Å MS

MeOH

RT, 24 h, 99%

intermediate structure

+

intermediate structure

NaOH, HCl

H2O, Buffer (pH = 5.5)

RT, 2 d, 75%

See the Petrenko-Kritschenko Piperidone Synthesis

intermediate structure

NaCl

DMF, H2O

Reflux, 4 h, 56%

See the Krapcho Decarboxylation

intermediate structure

Ph3P+CH3 Br-, n-BuLi

Et2O

RT to Reflux, 90 min, 82%

See the Wittig Reaction

intermediate structure

Pd/C, H2

1 atm

MeOH

RT, 8 h

intermediate structure

mCPBA

CH2Cl2

0 °C, 8 h, 64% (2 steps)

intermediate structure

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