Synthesis of Strychnine

Structure of Strychnine

C21H22N2O2

Principal investigator	Stephen F. Martin
Publication year	2001
Synthesis type	Formal
Number of steps	12 (linear)
References	J. Am. Chem. Soc. 2001, 123, 8003.

Part 1 of 1

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THF

-78 °C to RT, 2 h, 79%

See the Mannich Reaction

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Sealed tube

Mesitylene

160 °C, 72 h, 85%

See the Diels-Alder Reaction

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HClO4

H2O, THF

80 °C, 12 h, 93%

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Special reagent

(Ph3P)3RuCl2

PhMe

Reflux, 24 h, 79%

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Pd(OH)2/C, H2

1 atm

EtOAc, EtOH

RT, 5 h, 67%

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TsOH, NaOMe

MeOH

0 °C to RT, 30 h, 74%

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TBSCl, DMAP

Pyr

RT, 24 h, 71%

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Me3O+BF4-, 2,6-Di-tert-butylpyridine

MeOH

RT, 24.5 h, 83%

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t-BuOCl, SnCl4

PhMe

-15 °C, 60 min

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TMS2NLi

THF

-15 °C to RT, 3.5 h, 26%

See the Mannich Reaction

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HCl

H2O, MeOH

RT, ON, 83%

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Remaining...

34% (4 steps)

"See: J. Am. Chem. Soc. 1993, 115, 9293."

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