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 225 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

Phyllantidine

Chemical structure of Phyllantidine
C13H15NO3
Author Michael A. Kerr
Publication year 2006
Synthesis type Total synthesis
Number of steps 12 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
+
Chemical structure
+
Chemical structure
Yb(OTf)3
4Å MS
PhMe
RT to Reflux, ON, 86 %
Chemical structure
LiCl
DMSO, H2O
160 °C, 2 h, 85 %

See the Krapcho Decarboxylation
Chemical structure
Reagent structure
TMS2NK
THF
-78 °C, 2.5 h, 80 &

Selectivity : 75:25 dr
Chemical structure
LiAlH4
THF
0 °C, 2 h, 97 %

The major diastereoisomer was separated via its acetonide in (52 % yield).
Chemical structure
IBX
DMSO
RT, 2 h, 64 %
Chemical structure
VinylMgBr
THF
0 °C, 3 h, 76 %

See the Grignard Reaction
Chemical structure
IBX
DMSO
RT, 2 h, 79 %
Chemical structure
Grubbs catalyst (2nd gen.)
CH2Cl2
Reflux, 2 h, 74 %

See the Olefin Metathesis
Chemical structure
+
Chemical structure
DCC
CH2Cl2
RT, 60 min, 71 %
Chemical structure
K2CO3, 18-Crown-6
PhMe
RT, 2.5 h, 100 %

See the Horner-Wadsworth-Emmons Reaction
Chemical structure
DDQ
CH2Cl2, H2O
RT, ON, 98 %
Chemical structure
DIAD, Ph3P
PhH
RT, ON, 98 %

See the Mitsunobu Reaction
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