O-H Insertion

Huw Davies and co-worker at Emory have recently reported in JACS on the use of an alpha,alpha-diazo-benzyl methyl ester to a chiral tertiary alcohol using a secondary alcohol and a asymmetric rhodium dimer catalyst.  The reaction involves an O-H insertion step followed by a [2,3]-sigmatropic rearrangement.  This chemistry reminds us how Michael Doyle’s methodology is very important in the field.

JACS paper

Tandem Heterocyclization

Junliang Zhang and co-workers from East China Normal University have recently published in Chemistry – A European Journal on a novel transformation that involves the coupling between an an alpha,beta-unsaturated imine and an enynone substrate.

Chemistry A European Journal Paper

C-C Cleavage Via Mesylate Displacement

Johann Mulzer and co-workers at the University of Vienna have recently published in Chemistry – A European Journal on the lactone opening-decaboxylation via mesylate displacement to form homoallylic alcohols.

Chemistry – A European Journal paper

Cephalostatin Synthesis

Matthew Shair and co-workers at Harvard have recently published in JACS on the synthesis of cephalostatin, which consists of two steroids in its backbone. The coupling of the two steroid fragments involved a pyrazine ring formation.

JACS paper

[6+4] for CP structures

James Gleason and co-workers from McGill University in Canada have recently reported in Tetrahedron on a novel approach for the synthesis of CP molecules.  They used a cycloheptatrienone for a [6+4] reaction to form the bridged bicyclic component of the molecule.

Tetrahedron paper

Coprinastatin 1

George Pettit and co-workers at Arizona State University have recently published in the Journal of Natural Products on the isolation of coprinastatin 1 that was found from a cap fungus, Coprinus cinereus, which was growing on a small plant found in Shasta-Trinity National Forest, CA. It had an ED50 value of 5.3 micrograms/mL towards P388 lymphocytic leukemia cells.

JNP paper

Gold-Catalyzed C-H/C-C Activation

Yuxue Li and co-workers from the Shanghai Institute of Organic Chemistry have recently published in Org Lett on a cationic Au-catalyzed tandem C-H and C-C activation to convert vinyl cyclopropanes with saturated 6-membered rings to benzene rings.

OL paper

Reductive Coupling with Cobalt

Chien-Hong Cheng and co-workers at the National Tsinghua University in Taiwan have recently published in JACS on this interesting reaction.  At quick first glance I was thinking that this reaction had released cyanide and was wondering how the person who ran this reaction would survive on a large scale. Then I took a closer look and realized that it’s not cyanide the product is missing it’s just a single nitrogen from the nitrile starting material that becomes dissociated.  What’s interesting is that when they used acetonitrile they would obtain the cyclized product but when they used benzonitrile, the product would be acyclic.

JACS paper

Ru-Catalyzed C-H activation

Sylvain Darses and co-workers at CNRS have recently published in JOC on the C-H activation of the beta-position of enone substrates by coupling with a vinyl silane.

JOC paper

Peloruside B

Arun Ghosh and co-workers at Purdue University have recently reported in JOC on the biological activity and total synthesis of peloruside B in JOC.  They used a Yamaguchi macrolactonization to couple a carboxylic acid and a secondary alcohol to form the final macrolide structure.  Flow cytometry experiments were run to see the difference in the activities between the naturally isolated compound and the synthetically made one. The compound arrests cells in the G2M phase of the cell cycle.

JOC paper