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

Solandelactone E

Chemical structure of Solandelactone_E
C22H34O4
Author Varinder K. Aggarwal
Publication year 2010
Synthesis type Total synthesis
Number of steps 17 (3 parts)
Reference

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
AllylBr, In
THF
0 °C to RT, 4 h, 77%
Chemical structure
t-BuOOH, Ti(Oi-Pr)4, (-)-DET
4 Å MS
CH2Cl2
-20 °C, 5 h, 75%

Selectivity : 97:03 er
See the Sharpless Epoxidation
Chemical structure
PhSO2Cl, Et3N, DMAP
CH2Cl2
0 °C to RT, 60 min, 90%
Chemical structure
TMS2NNa, MeCN
THF
-78 to 0 °C, 3 h, 77%

Also isolated was the C1-epimer (14 % yield).
Chemical structure
3,4-Dihydropyran, Pyr.TsOH
CH2Cl2
RT, ON, 94%
Chemical structure
K2OsO2(OH)4, NaIO4, 2,6-Lutidine
Dioxane , H2O
RT

See the Lemieux-Johnson Oxidation
Chemical structure + Chemical structure
TMS2NNa
THF
-78 °C to RT, ON, 59% (2 steps)

Selectivity : 90:10 Z/E
See the Wittig Reaction
Aqueous HCl work-up cleaves the THP.
Chemical structure
Reagent structure
Et3N
THF
0 °C to RT, 4 h

Ar = 2,4,6-trichlorophenyl
Chemical structure
DMAP
PhMe
60 to 90 °C, 34 h, 79% (2 steps)

See the Yamaguchi Esterification
Ar = 2,4,6-trichlorophenyl
Chemical structure
Ni (Raney), NaH2PO2
Pyr, H2O, AcOH
0 °C to RT, 4 h, 87%
Chemical structure

Report an error in this part

Part 2 of 3
Chemical structure
+
Chemical structure
NaH
THF
Reflux, 24 h, 85%
Chemical structure
  1. s-BuLi
  2. Bu3SnCl
Et2O
-78 °C to RT, ON, 42%

Selectivity : 91:09 R/S
The yield was 84 % brsm.
Chemical structure
HCl, NaIO4
MeOH, H2O
RT
Chemical structure + Chemical structure
TMS2NNa
THF
-78 °C to RT, ON, 80% (2 steps)

See the Wittig Reaction
Chemical structure

Report an error in this part

Part 3 of 3
Chemical structure
+
Chemical structure
+
Chemical structure
n-BuLi, (CH2NMe2)2
Et2O
-78 °C to RT, 2.5 h, 73%
Chemical structure
t-BuOOH, Ti(Oi-Pr)4
CH2Cl2
-10 °C, 5.5 h
Chemical structure
AcOH
MeOH
0 °C, ON, 68% (2 steps)
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