Naturalproductman’s Blog

Hey, is that a natural product?!

Archive for February, 2010

Copper Cascade

Posted by naturalproductman on February 25, 2010

Andrei Yudin and co-worker at the University of Toronto have recently published in Chemistry – A European Journal on a nice domino process.

domino

Chemistry – A European Journal paper

Advertisements

Posted in Cascade Reactions, Copper, Methodology, Pericyclic reactions, Transition Metal | Leave a Comment »

Enzyme Analog Studies

Posted by naturalproductman on February 25, 2010

Derrek Tan and co-workers at Sloan Kettering have recently published in JACS on a study focused on looking at an enzyme that forms a tetrahedral intermediate with a cysteine residue on the enzyme and later gets released, ie:  the thiol group attacks the carbonyl on the substrate and later releases.  In their study, they have made an analog of the substrate that will covalently bind to the thiol group and not get released – basically making the covalent linkage irreversible by converting the carbonyl moiety into a Michael acceptor.

analog

JACS paper

Nature paper

Posted in Chemical Biology, Conjugate Additions, Methodology, Michael, Named Reactions | Leave a Comment »

Double Benzylation via C-H Activation

Posted by naturalproductman on February 25, 2010

Masahiro Miura and co-workers at Osaka University have recently published in Organic Letters on a C-H functionalization process that introduces a benzyl group to benzoxazoles in the presence of a base.  They further benzylate the the product by the same reaction conditions but without a base in the second step.

benzylation

OL paper

Posted in C-H activation, Cascade Reactions, Methodology, Palladium, Transition Metal | Leave a Comment »

JBIR-22

Posted by naturalproductman on February 24, 2010

Kazuo Shin-ya and co-workers at National Institute of Advanced Industrial Science and Technology in Japan have recently published in the Journal of Natural Products of the isolation of JBIR-22.  This pyrrolidinedione was found to be an analogue of equisetin, which has protein protein interaction inhibitory qualities.  They isolated the species that produced this compound (Verticillium sp. f21794) by treating the soil sample with anthracycline antibiotic, daunomycin, which helped them isolate the slower growing fungi from a mix of fast- and slow-growing fungi.

jbir-22

JNP paper

Posted in Trophy Targets | Leave a Comment »

Shinalactone A

Posted by naturalproductman on February 24, 2010

Han-Dong Sun and co-workers at the Chinese Academy of Sciences have recently published in Organic Letters on a new cytotoxic triterpenoid called shinalactone A.  It had 5.9 micromolar IC50 value against PANC-1 human cancer cell line.

shinalactone
OL paper

Posted in Seven-Membered Rings, Triterpenoids | Leave a Comment »

Prins-Schmidt Cascade

Posted by naturalproductman on February 23, 2010

Jeffrey Aube and co-workers from the University of Kansas have recently published in Organic Letters on a tandem Prins/Schmidt reaction mediated by titanium tetrachloride to access the a 5,6,6-tricyclic ring system belonging to some alkaloids – cyclindricine and lepadiformine (diastereomers).

prins


OL paper

Posted in Cascade Reactions, Methodology, Named Reactions, Prins, Schmidt, Titanium, Transition Metal | Leave a Comment »

Diels Alder with a Boronic Acid

Posted by naturalproductman on February 23, 2010

Carmen Carreno and co-workers at Universidad Autónoma de Madrid Cantoblanco have recently published in Chemistry a European Journal on a Diels Alder reaction that involves the use of substituted 2-quinonyl boronic acids as the dienophile.

diels alder

Chemistry a European Journal paper

Posted in Cascade Reactions, Diels-Alder, Methodology, Named Reactions | Leave a Comment »

C-C Bond Coupling via Decarboxylation

Posted by naturalproductman on February 23, 2010

Francois Bilodeau and co-workers at Boehringer Ingelheim in Canada have recently published on a decarboxylative coupling between heteroaromatic carboxylic acids and aryl halides using a palladium catalyst.
pd

JOC paper

Posted in cross coupling, Methodology, Palladium, Transition Metal | Leave a Comment »

DKR with Aza-Cope Rearrangement

Posted by naturalproductman on February 22, 2010

Larry Overman and co-workers at UC Irvine have recently published in JACS on a dynamic kinetic resolution via an Aza-Cope rearrangement.

aza cope


JACS paper

Posted in Aza-Cope rearrangement, Cascade Reactions, Methodology, Named Reactions | Leave a Comment »

Rh-Catalyzed [5+2]

Posted by naturalproductman on February 21, 2010

Chisato Mukai and co-workers at Kanazawa University have recently published in ACIEE on a rhodium catalyzed [5+2] reaction.

5+2

ACIEE paper

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