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Archive for February, 2010

Diazonamide Synthesis

Posted by naturalproductman on February 28, 2010

Tarek Sammakia and co-workers at the University of Colorado at Boulder have recently published in ACIEE on a formal synthesis of diazonamide.  The key cyclization process involved an SnAr reaction, which displaces a bromide on the oxazole group.

snar

ACIEE paper

Posted in Alkaloids, Aromatic, Cascade Reactions, Conjugate Additions, Methodology | Leave a Comment »

Synthesis of Echinopines A and B

Posted by naturalproductman on February 28, 2010

David Chen and co-workers at Institute of Chemical and Engineering Sciences in Singapore have recently published in JACS on the synthesis of echinopines where the key reactions involved the use of an alpha-diazo carbonyl intermediate to afford a cyclopropane ring and an SmI2-mediated intramolecular pinacol coupling between an aldehyde and ketone to form a seven membered ring.

echinopines

JACS paper

Posted in Cascade Reactions, Methodology, Rhodium, Ring forming, Seven-Membered Rings, Transition Metal | 2 Comments »

Bafilomycins

Posted by naturalproductman on February 27, 2010

Raymond Andersen’s group at the University of British Columbia have recently published on the isolation of a thiomorpholine containing bafilomycin.

bafilomycin


JNP paper

Posted in Macrolides | Leave a Comment »

Access to beta-Unsubstituted Enones

Posted by naturalproductman on February 27, 2010

Brian Connell and co-workers at Texas A&M have recently published in Chemical Communications on a methylenation process that leads to alpha,beta-unsaturated enones, enals, from ketones and aldehydes.

enones

Chemical Communications paper

Posted in Methodology | Leave a Comment »

Palladium Catalyzed Multi Component Reaction

Posted by naturalproductman on February 27, 2010

Bartolo Gabriele and co-workers at Università della Calabria in Italy have recently published in Tetrahedron Letters on a palladium catalyzed four component process that leads to substituted furans.

furans

TL paper

Posted in Cascade Reactions, Methodology, Palladium, Transition Metal | Leave a Comment »

Three Component Coupling for Substituted Pyridines

Posted by naturalproductman on February 26, 2010

Ken Tanaka and co-workers at the Tokyo University of Agriculture and Technology have recently published in Organic Letters on a method to make substituted pyridines from two aryl ethynyl ethers and an isocyanate using a rhodium catalyst.

mcc

OL paper

Posted in Cascade Reactions, Methodology, Multi-Component Coupling, Rhodium, Transition Metal | Leave a Comment »

Platinum Cascade Cyclization

Posted by naturalproductman on February 26, 2010

Chang Ho Oh and Hanyang University have recently published in Organic Letters  on a platinum catalyzed cyclization process of an enynylbenzaldehyde.

enynyl benzaldehyde

OL paper

Posted in Methodology, Platinum, Transition Metal | Leave a Comment »

Multicomponent Coupling with Palladium

Posted by naturalproductman on February 26, 2010

Norio Sakai and co-workers at the Tokyo University of Science have recently published in Organic Letters on a multi-component reaction that involves the coupling between two alkynes and an aryl halide using a palladium catalyst.
palladium

OL paper

Posted in Cascade Reactions, Methodology, Multi-Component Coupling, Palladium, Transition Metal | Leave a Comment »

Vindoline

Posted by naturalproductman on February 26, 2010

Dale Boger and co-workers have published in JACS on a nice synthesis of vindoline that looks like his previous synthesis of fendleridine.  However, it’s worth looking at considering the generality of this awesome reaction.

vindoline


JACS paper

Posted in Alkaloids, Methodology, Pericyclic reactions | Leave a Comment »

C-H Activation with Magnesium

Posted by naturalproductman on February 25, 2010

We always hear about transition metal catalyzed C-H insertions.  Well here’s a C-H activation mechanistic study with magnesium from the labs of Detlef Schröder and co-workers at the Academy of Sciences of the Czech Republic.

mg

Chemistry a European Journal paper

Posted in C-H activation, Methodology | Leave a Comment »

 
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