Synthesis of Strychnine

C21H22N2O2

Principal investigator	Martin E. Kuehne
Publication year	1993
Synthesis type	Total
Number of steps	19 (linear)
References	J. Org. Chem. 1993, 58, 7490.

Part 1 of 1

BnBr, K2CO3

MeOH

Reflux, 3 d, 89%

t-BuOCl, Et3N

THF

-78 °C, 2.5 h

THF

-78 °C to RT, 13 h, 83% (2 steps)

See the Mannich Reaction

LiCl, Et3N.HCl

DMA

130 °C, 2.5 h, 84%

See the Krapcho Decarboxylation

H2, Pd/C

1 atm

AcOH

RT, 87%

BF3.OEt2

4 Å MS, Dean-Stark

PhMe

Reflux, 18 h

See the Pictet-Spengler Reaction

HClO4

H2O, THF

0 °C to RT, 5 h, 51% (2 steps)

n-BuLi, Me3S+ I-

THF

-20 °C to RT, 4 h, 70%

See the Johnson-Corey-Chaykovsky Reaction

DBU
H2 , Pd/C

1 atm

MeOH

RT to Reflux, 12 h, 70% (2 steps)

NaBH3CN

AcOH

RT, 30 min

Ac2O

Pyr

RT, 10 h, 83% (2 steps)

TMS2NLi

THF

Reflux, 30 min

See the Claisen Condensation

NaBH4

AcOH, MeOH

0 °C, 60 min, 64% (2 steps)

Ac2O

Pyr

RT, ON, 98%

DBU

Dioxane , H2O

Reflux, 10 h, 61%

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C to RT, 2 h, 98%

See the Swern Oxidation

TMS2NK, 																	
																						(EtO)2P(O)CH2CO2Me

																	THF															

								RT, 								2.5 h, 								39%
							
								See the Horner-Wadsworth-Emmons Reaction
							
								"Also isolated was the Z-isomer (42 % yield) which could be photoisomerized to the desired product."

BF3.OEt2, i-Bu2AlH

CH2Cl2

-78 °C, 4.5 h, 87%

KOH

EtOH

Reflux, 6 h, 28%

"The yield was 72 % brsm."

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