Naturalproductman’s Blog

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Archive for July, 2010

Ring Expansion via Stevens Rearrangement

Posted by naturalproductman on July 31, 2010

Maria Valpuesta and co-workers from the Universidad de Malaga have published in the European Journal of Organic Chemistry on a Stevens rearrangement approach to synthesize substituted benzazepines.

stevens

EUropean JOC paper

Posted in Cascade Reactions, Methodology, Named Reactions, Ring expansion, Stevens rearrangement | Leave a Comment »

1,3-Dipolar Cycloaddition

Posted by naturalproductman on July 31, 2010

Mehdi Ghandi and co-workers at the University of Tehran have published in Tetrahedron on a 1,3-dipolar cycloaddition process between 3-acetyl coumarins and isatin.  What’s interesting is the solvent  determines if there is a deacetylation – in the case of methanol you lose the acyl group and in toluene, the acetyl remains in tact.

1,3 dipolar cycloaddition


Tetrahedron paper

Posted in Cascade Reactions, Cycloaddition, Methodology, Pericyclic reactions, Spirocycles | Leave a Comment »

Hydrovinylation accross Dienes

Posted by naturalproductman on July 31, 2010

Dieter Vogt has published in ACIEE on a catalytic asymmetric hydrovinylation of 1,3-dienes using cobalt.

hydrovinylation

ACIEE paper

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

Four to Five Ring Expansion

Posted by naturalproductman on July 29, 2010

Jason Kingsbury and co-workers from Boston College have published in Organic Letters on the use of TMS-diazomethane to expand a cyclobutanone to a cyclopentanone.

ring expansion

OL paper

Posted in Cascade Reactions, Methodology, Ring expansion, Scandium, Transition Metal | Leave a Comment »

Englerin A Synthesis

Posted by naturalproductman on July 29, 2010

Emmanuel Theodorakis and co-workers at UCSD have published in Organic Letters on a synthesis of englerin A where they used a rhodium catalyzed [4+3] reaction between a furan and an alpha-diazoester to obtain the seven membered ring.

rhodium

OL paper

Posted in Asymmetric, Cascade Reactions, Methodology, Rhodium, Sesquiterpenes, Seven-Membered Rings, Transition Metal | Leave a Comment »

Didehydroxylation with Rhenium

Posted by naturalproductman on July 29, 2010

Dihydroxylations of olefins is a common technique to make 1,2-diols – however, recently in JACS, the Bergman and Ellman team have published on the reverse reaction using a rhenium catalyst.

didehydroxylation

JACS paper

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

Oil Sponge

Posted by naturalproductman on July 29, 2010

George John and co-workers at CUNY are designing small molecules that will sequester oil from water.

oil spill

ACIEE paper

Posted in Environmental, Methodology | Leave a Comment »

Copper Catalyzed C-H

Posted by naturalproductman on July 29, 2010

Felix Tuczek and co-workers at Christian-Albrechts-Universität zu Kiel have published in ACIEE on a copper catalyzed C-H oxidation of phenols.

oxidation

ACIEE paper

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

Baculiferins A-O

Posted by naturalproductman on July 27, 2010

Wenhan Lin and co-workers from Peking University have published on the isolation of some pyrrole alkaloids.  Baculiferin M had an IC50 of 0.2 micrograms/mL against HIV-1 IIIB virus expressed in MAGI cells.

baculiferins

Bioorganic and Medicinal Chemistry paper

Posted in Alkaloids, Diseases, HIV | Leave a Comment »

Ugi then Staudinger-Aza-Wittig

Posted by naturalproductman on July 27, 2010

Tomas Torroba and co-workers from the Universidad de Burgos have published on an Ugi reaction followed by a Staudinger-Aza-Wittig cyclization.  The key was that the carboxylic acid partner in the Ugi reaction was tethered by an azide group.

cascade

Tetrahedron paper

Posted in Aza-Wittig, Cascade Reactions, Methodology, Named Reactions, Staudinger, Ugi | Leave a Comment »

 
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