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Strychnine

"Dedicated to Professor Rolf Huisgen on the occasion of his 90th birthday"

Chemical structure of Strychnine

Author	Hans-Ulrich Reissig
Publication year	2010
Synthesis type	Formal synthesis
Number of steps	10 (linear)
Reference	Angew. Chem. Int. Ed. 2010, 49, 8021.

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Part 1 of 1

Chemical structure

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Chemical structure

Et₃N, DMAP

CH₂Cl₂
RT, 3 d, 82 %

Chemical structure

SmI₂, BrCH₂CN

THF, HMPA
RT, ON, 77 %

Chemical structure

H₂, Ni (Raney)
1 atm

MeOH
RT, 3 d, 97 %

Chemical structure

ClCO₂Me, Et₃N, DMAP

CH₂Cl₂
RT, 4 h, 87 %

Chemical structure

MsCl, Et₃N, DMAP, DBU

CH₂Cl₂
RT, 48 h, 63 %

Chemical structure

TMSI

CHCl₃
Reflux, 2 h

Chemical structure

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Chemical structure

K₂CO₃, n-Bu₄N⁺ I^-

MeCN
RT, ON, 65 % (2 steps)

Chemical structure

Pd(OAc)₂, K₂CO₃, n-Bu₄N⁺ Cl^-

DMF
70 °C, 4 h, 68 %

See the Heck Coupling

Chemical structure

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Remaining...

27 % (2 steps)

See : J. Org. Chem. 1994, 59, 2685; J. Org. Chem. 1993, 58, 7490.

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