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 Masakatsu Shibasaki
Publication year 2002
Synthesis type Total synthesis
Number of steps 31 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
Reagent structure
Dimethyl malonate, KOt-Bu
4Å MS
THF
4 °C to RT, 24 h, 91%

Selectivity : >99:01 er
See the Michael Addition
Chemical structure
2-Ethyl-2-methyl-1,3-dioxolane, TsOH
RT, 16 h
Chemical structure
LiCl
DMSO, H2O
140 °C, 17 h, 97% (2 steps)

See the Krapcho Decarboxylation
Chemical structure + Chemical structure
i-Pr2NLi
THF
-78 °C, 19 h, 72%

See the Claisen Condensation
The yield was 82 % brsm.
Chemical structure
NaBH3CN, TiCl4
THF, CH2Cl2
-78 to -55 °C, 10.5 h
Chemical structure
DCC, CuCl
PhH
Reflux, 5 h, 70% (2 steps)

Selectivity : >94:06 dr
Chemical structure
i-Bu2AlH
CH2Cl2
-78 °C, 60 min
Chemical structure
TIPSOTf, Et3N
CH2Cl2
-78 °C, 10 min, 98% (2 steps)
Chemical structure
Camphorsulfonic acid
Acetone
RT, 2 d, 62%

The yield was 90 % brsm.
Chemical structure
LiTMP, TMSCl
THF
-78 °C, 2 h
Chemical structure
Pd2(dba)3.CHCl3, Diallyl carbonate
MeCN
RT, 12 h, 90% (2 steps)

See the Saegusa-Ito Oxidation
Chemical structure
i-Pr2NLi, TMSCl
THF
-78 °C, 2 h
Chemical structure
CH2O, Yb(OTf)3
THF, H2O
RT, 3 d

See the Mukaiyama Aldol Addition
Chemical structure
DBU
CH2Cl2
RT, 60 min, 57% (3 steps)
Chemical structure
I2, DMAP
CH2Cl2
RT, 5 h, 89%
Chemical structure + Chemical structure
Pd2(dba)3.CHCl3, Ph3As, CuI
DMF
RT, 48 h, 100%

See the Stille Coupling
Chemical structure
TMS(CH2)2OCH2Cl, i-Pr2NEt
CH2Cl2
4 °C to RT, 24 h, 100%
Chemical structure
Et3N.3HF
THF
RT, 2.5 d, 100%
Chemical structure + Chemical structure
Tf2O, i-Pr2NEt
CH2Cl2
-78 °C, 90 min

See the Michael Addition
Chemical structure
Zn, NH4Cl
MeOH, H2O
RT, 2 h, 77% (2 steps)
Chemical structure
Me2SSMe+ BF4-
4Å MS
CH2Cl2
RT, 3 h, 86%
Chemical structure
NaBH3CN, TiCl4
THF, CH2Cl2
-78 °C, 65 min, 68%
Chemical structure
HCl
MeOH, H2O
55 °C, 3 h
Chemical structure
Ac2O
Pyr
RT, 36 h
Chemical structure
NaOMe
MeOH
RT, 30 min
Chemical structure
TIPSCl, Imidazole
DMF, CH2Cl2
4 °C, 2 h, 51% (4 steps)
Chemical structure
NiCl2, NaBH4
EtOH, MeOH
RT, 40 min, 33%

The yield was 94 % brsm.
Chemical structure
Pyr.SO3, Et3N
DMSO
RT, 60 min

See the Parikh-Doering Oxidation
Chemical structure
Et3N.3HF
THF
RT, 12 h, 83% (2 steps)
Chemical structure
NaOMe
MeOH
40 °C, 2 d
Chemical structure
Malonic Acid, NaOAc
AcOH, Ac2O
110 °C, 2 h, 42% (2 steps)

See the Aldol Addition
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