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

Cylindrospermopsin

Chemical structure of Cylindrospermopsin
C15H21N5O7S
Author Barry B. Snider
Publication year 2000
Synthesis type Total synthesis
Number of steps 24 (3 parts)
Reference

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
PCl5, POCl3
Reflux, 2 d
Chemical structure
MeOH
0 °C to RT, 12 h, 57% (2 steps)
Chemical structure
LiBH4
THF, EtOH
RT, 2 h, 93%
Chemical structure
Dess-Martin Periodinane
CH2Cl2
RT, 60 min, 90%

See the Dess-Martin Oxidation
Chemical structure

Report an error in this part

Part 2 of 3
Chemical structure
+
Chemical structure
ClCO2CH2CCl3
THF
-30 °C, 2.5 h, 49%

The yield was 87 % brsm.
Chemical structure
  1. VinylMgBr, CuBr.Me2S
  2. TMSCl
THF
-78 °C, 2 h, 92%

See the Michael Addition
Chemical structure
Zn
CH2Cl2, AcOH
RT, 5 h, 96%
Chemical structure
Li(s-Bu)3BH
THF
-78 °C, 2 h, 94%
Chemical structure
ClCO2Bn, Na2CO3
THF
RT, ON, 96%
Chemical structure
TBSCl, Imidazole, DMAP
CH2Cl2
RT, ON, 89%
Chemical structure

Report an error in this part

Part 3 of 3
Chemical structure
+
Chemical structure
EtMgBr
THF
0 °C to RT, 4 h, 69%

See the Grignard Reaction
The yield was 83 % brsm.
Chemical structure
TBSCl, Imidazole
CH2Cl2
RT, 5 h, 88%
Chemical structure
  1. O3
  2. Me2S
CH2Cl2
-78 °C, 20 min, 72%
Chemical structure
BnNH2, NaBH3CN, Na2SO4
PhMe, MeOH, AcOH
RT, 4 h, 68%
Chemical structure
H2, Pd/C
1 atm
MeOH
RT, ON
Chemical structure
BrCN
PhMe
RT, 5 h
Chemical structure
NaH, ClCO2Bn
THF
0 °C to RT, 8 h, 45% (3 steps)
Chemical structure
n-Bu4N+ F-
THF
RT, ON, 83%
Chemical structure
MnO2
CH2Cl2
RT, 60 min, 87%
Chemical structure
Ac2O
Pyr
RT, ON, 87%

Selectivity : 83:17
Chemical structure
+
Chemical structure
CuBr2
EtOAc
35 °C, 20 min
Chemical structure
H2, Pd(OH)2/C
1 atm
MeOH
RT, 8 h, 42% (2 steps)

Also isolated was the C7-epimer (28 % yield).
Chemical structure
HCl
H2O
100 °C, 6 h, 95%
Chemical structure
SO3.DMF, Na2SO4
Pyr
RT, ON, 50-70%
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