Synthesis of Strychnine

Structure of Strychnine

C21H22N2O2

Principal investigator	Larry E. Overman
Publication year	1993
Synthesis type	Total
Number of steps	24 (linear)
References	J. Am. Chem. Soc. 1993, 115, 9293.

Part 1 of 1

intermediate structure

+

intermediate structure

Ph3P, Pd2(dba)3, NaH

THF

RT, 91%

See the Tsuji-Trost Reaction

intermediate structure

TiCl4, NaBH3CN

THF

-78 °C, 98%

intermediate structure

+

intermediate structure

DCC, CuCl

PhH

80 °C, 91%

intermediate structure

i-Bu2AlH

CH2Cl2

-78 °C

intermediate structure

1,1,3,3-Tetramethylguanidine, TIPSCl

NMP

-10 °C, 65% (2 steps)

intermediate structure

CrO3, H2SO4

Acetone, H2O

-5 °C, 97%

See the Jones Oxidation

intermediate structure

Li(s-Bu)3BH
PhNTf2

THF

-78 to 0 °C, 88%

intermediate structure

Pd(PPh3)4, LiCl, (Me3Sn)2

THF

60 °C, 80%

See the Stille Coupling

intermediate structure

+

intermediate structure

Ph3As, Pd2(dba)3, LiCl, CO

3.5 atm

NMP

70 °C, 80%

See the Stille Coupling

intermediate structure

Me3N+Bn HO-, t-BuOOH

THF

-15 °C, 91%

See the Michael Addition

intermediate structure

Ph3P=CH2

THF

0 °C to RT, 92%

See the Wittig Reaction

intermediate structure

n-Bu4N+ F-

THF

-15 °C, 100%

intermediate structure

MsCl, i-Pr2NEt

CH2Cl2

-23 °C

intermediate structure

LiCl

RT

See the Finkelstein Reaction

intermediate structure

NaH, CF3CONH2

DMF

RT

intermediate structure

NaH

PhH

100 °C

intermediate structure

KOH

EtOH, H2O

60 °C, 43% (5 steps)

intermediate structure

(CH2O)n, Na2SO4

MeCN

80 °C, 98%

See the Cope Rearrangement

intermediate structure

i-Pr2NLi
MeO2CCN

THF

-78 °C

See the Claisen Condensation

intermediate structure

HCl

MeOH

Reflux, 70% (2 steps)

intermediate structure

Zn, H2SO4

H2O, MeOH

Reflux

intermediate structure

NaOMe

MeOH

RT

intermediate structure

i-Bu2AlH

CH2Cl2

-78 °C, 52% (3 steps)

intermediate structure

NaOAc, Malonic Acid, Ac2O

AcOH

110 °C, 65%

intermediate structure

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