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

Suaveoline

"Dedicated to Elmer Fike on the occasion of his 70th birthday."

Chemical structure of Suaveoline
C20H21N3
Author James M. Cook
Publication year 1989
Synthesis type Total synthesis
Number of steps 20 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
Na, MeI
NH3
Chemical structure
HCl
MeOH
Reflux

See the Fischer Esterification
Chemical structure
PhCHO, NaBH4
MeOH
73% (3 steps)
Chemical structure + Chemical structure
PhH, Dioxane
Reflux

See the Pictet-Spengler Reaction
Chemical structure
HCl
MeOH
Reflux, 88% (2 steps)

See the Fischer Esterification
Chemical structure
NaH
PhMe, MeOH
Reflux

See the Dieckmann Condensation
Chemical structure
HCl
AcOH
Reflux, 83% (2 steps)
Chemical structure
PhSOCH2Cl, i-Pr2NLi
THF
-78 °C
Chemical structure
KOH
THF, H2O
RT, 24 h, 95% (2 steps)
Chemical structure
LiClO4, n-Bu3PO
PhMe
Reflux, 60 min, 80%
Chemical structure
LiAlH4
Et2O
-20 °C, 91%
Chemical structure + Chemical structure
2,4,6-Trimethylbenzoic acid
125 °C, 3 h, 79%

Selectivity : 93:07 R/S (C3)
See the Johnson-Claisen Rearrangement
Chemical structure
LiAlH4
Et2O
-20 °C
Chemical structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C

See the Swern Oxidation
Chemical structure
(CH2OH)2, TsOH
PhH
Reflux, 60% (3 steps)
Chemical structure
  1. 9-BBN
  2. H2O2, NaOH, H2O
THF
35 °C, 60 min, 91%
Chemical structure
(PhSeO)2O
PhCl
120 °C, 15 min, 58%
Chemical structure
HCl
THF, H2O
RT, 24 h
Chemical structure
NH2OH.HCl
EtOH
Reflux, 40% (2 steps)
Chemical structure
H2, Pd/C
MeOH
69%
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