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

Gymnomitrol

Chemical structure of Gymnomitrol
C15H24O
Author Leo A. Paquette
Publication year 1979
Synthesis type Total synthesis
Number of steps 13 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
(CH2OH)2, TsOH
PhH
Reflux, 95%
Chemical structure
NH2NH2, KOH
Ethylene Glycol
Reflux, 82%

See the Wolff-Kishner Reduction
Chemical structure
No experimental details were reported for this step.
Chemical structure
(CH2O)3, PhNHMe.TFA
Dioxane
45%

See the Claisen-Schmidt Condensation
The yield was 90 % brsm.
Chemical structure + Chemical structure
  1. CuBr.Me2S
  2. MeI
HMPA
66%

See the Michael Addition
Chemical structure
mCPBA
CH2Cl2
74%

See the Prilezhaev Reaction
Chemical structure
H2SO4
MeOH
Reflux, 24 h, 74%

Selectivity : 55:45
Also isolated was the desired aldol product (22% yield, see the next two steps).
Chemical structure
+
Chemical structure
H2O
AcOH
74%
Chemical structure
KOH
MeOH
2.5 d, 26%

See the Aldol Addition
The yield was 61 % brsm.
Chemical structure
CrO3, H2SO4
Acetone
89%

See the Jones Oxidation
Chemical structure
MeLi
-78 °C, 70%
Chemical structure
POCl3
Pyr
Reflux, 2 h, 70%

Selectivity : 50:50
Chemical structure
+
Chemical structure
LiAlH4
THF
0 °C, 45%
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