Synarchive logo
Google+ Facebook Twitter RSS Feed
Support this website
Synarchive is free but requires a lot of work. If you enjoy and find it useful, please support us by making a donation.
Named reactions

Get references and more from over 229 named organic chemical reaction

Go to the named reaction index

Protecting Groups

Get the conditions needed to install/remove a wide range of protecting groups.

Go to the protecting groups index

Search synthesis

Strychnine

Chemical structure of Strychnine
C21H22N2O2
Author Martin E. Kuehne
Publication year 1993
Synthesis type Total synthesis
Number of steps 19 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
BnBr, K2CO3
MeOH
Reflux, 3 d, 89%
Chemical structure
t-BuOCl, Et3N
THF
-78 °C, 2.5 h
Chemical structure + Chemical structure
THF
-78 °C to RT, 13 h, 83% (2 steps)

See the Mannich Reaction
Chemical structure
LiCl, Et3N.HCl
DMA
130 °C, 2.5 h, 84%

See the Krapcho Decarboxylation
Chemical structure
H2, Pd/C
1 atm
AcOH
RT, 87%
Chemical structure + Chemical structure
BF3.OEt2
4 Å MS, Dean-Stark
PhMe
Reflux, 18 h

See the Pictet-Spengler Reaction
Chemical structure
HClO4
THF, H2O
0 °C to RT, 5 h, 51% (2 steps)
Chemical structure
Me3S+ I-, n-BuLi
THF
-20 °C to RT, 4 h, 70%

See the Johnson-Corey-Chaykovsky Reaction
Chemical structure
  1. DBU
  2. H2, Pd/C
1 atm
MeOH
RT to Reflux, 12 h, 70% (2 steps)
Chemical structure
NaBH3CN
AcOH
RT, 30 min
Chemical structure
Ac2O
Pyr
RT, 10 h, 83% (2 steps)
Chemical structure
TMS2NLi
THF
Reflux, 30 min

See the Claisen Condensation
Chemical structure
NaBH4
AcOH, MeOH
0 °C, 60 min, 64% (2 steps)
Chemical structure
Ac2O
Pyr
RT, ON, 98%
Chemical structure
DBU
Dioxane , H2O
Reflux, 10 h, 61%
Chemical structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 2 h, 98%

See the Swern Oxidation
Chemical structure
(EtO)2P(O)CH2CO2Me, TMS2NK
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.
Chemical structure
i-Bu2AlH, BF3.OEt2
CH2Cl2
-78 °C, 4.5 h, 87%
Chemical structure
KOH
EtOH
Reflux, 6 h, 28%

The yield was 72 % brsm.
Chemical structure

Report an error in this part

comments powered by Disqus
homepage - authors - molecules - named reactions - protecting groups - advanced search - contact
© 2011-2017 SynArchive