Removing triphenylphosphine oxide

I have had this silly problem in trying to get rid of triphenylphosphine oxide from my reaction mixture.  It’s stuck with my final product and can be a pain.  Some tricks I’ve seen are the use of dissolving mixture (O=PPh3 and product) in ether and run through short pad of silica.  This would be great if my product weren’t so polar – instead my product does not elute with ether.  Another trick was from this Lipshutz paper in 2003 where they used Merrifield resin to scavenge the phosphine.

 

OL paper

2D-IR spectroscopy

Robin Hoschstrasser and co-workers at UPenn have reported in Science on the use of 2D-IR spectroscopy to get the structure of a protein.

 

Science paper

Synthesis of Goniomitine

Jerome Waser and co-workers at Ecole Polytechnique Fédérale de Lausanne in Switzerland have published on a cyclopropane ring opening  strategy to synthesize goniomitine.  The strategy was to use a vinyl cyclopropyl ketone and open the cyclopropane with pTsOH to generate a precursor for a homo-Nazarov cyclization to access the six membered ring fused with the indole ring.

ACIEE paper

It’s not Delivery, it’s HNPO.

Shouheng Sun from Brown University has recently published in JACS on a target delivery of cisplatin to cancer cells using porous hollow nanoparticles (PHNP).  They concluded that the nanoparticles deliver the cisplatin better at 2.9 micromolar IC50 towards breast cancer SK-BR-3 while without the nanoparticles, it’s activity is 6.8 micromolar. 

JACS link

TTN Ring Contraction

The ring contraction reaction is a pretty neat trick using a thallium reagent published by University of Basel in Switzerland and University of Sao Paulo in Brazil by Andreas Pfaltz and Luiz Silva and co-workers in JOC.

JOC paper

A review on ring contractions by Silva can be found in TL:
TL Review

A Tandem Hydroalkoxylation-Hydroarylation Reaction

Francisco J. Fananas at the Universidad de Oviedo in Spain has recently published a synthesis on bruguierol A, which is a natural product that shows modest antimicrobial activity.  The activity is okay, but the way they made the bicyclic ring system is really neat and worth checking out.

The JOC paper here

Isolation paper