Naturalproductman’s Blog

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Archive for March, 2011

Chloroform in Barton Decarboxylation

Posted by naturalproductman on March 25, 2011

John Tsanaktsidis and co-workers at CSIRO in Australia have reported in Organic Letters on a Barton decarboxylation protocol using chloroform as the hydrogen source.

Barton

 

OL paper

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Posted in Cascade Reactions, Methodology, Radical Chemistry | Leave a Comment »

DFT with NMR

Posted by naturalproductman on March 25, 2011

Alessandro Bagno and co-workers at Universitat Padova have reported in JACS on the use of density functional theory and NMR to assign the stereochemistry to vannusal B.

NMR

 

JACS paper

Posted in Computational, Polycyclic, Terpenoids | Leave a Comment »

Polyketides – daeschol A, dalmanol A and acetodalmanols A and B

Posted by naturalproductman on March 25, 2011

Ren Tan and co-workers from Nanjing University have reported in JACS on the isolation of a set of polyketides.

polyketide

JACS paper

Posted in Polyketides | Leave a Comment »

Z-selective Olefin Metathesis

Posted by naturalproductman on March 24, 2011

Hoveyda and co-workers at Boston College have reported in Nature on a Z-selective olefin metathesis reaction.

 

Nature paper

Posted in Carbene, Metathesis, Methodology, Molybdenum, Transition Metal | Leave a Comment »

Amidine Synthesis

Posted by naturalproductman on March 23, 2011

Nobutaka Fujii and co-workers from Kyoto University have reported in Organic and Biomolecular Chemistry on the transformation of an amidoxime to an amidine unit.

amidine
OBC paper

Posted in Cascade Reactions, Methodology, Peptides | Leave a Comment »

Gold Catalyzed Gostelli-Claisen

Posted by naturalproductman on March 23, 2011

Martin Hiersemann and co-workers at Universitat Dortmund have reported in Organic Letters on a gold catalyzed Gosteli-Claisen rearrangement.

gold

 

OL paper

Posted in Cascade Reactions, Claisen rearrangement, Gold, Methodology, Named Reactions, Pericyclic reactions, Sigmatropic Rearrangements, Transition Metal | Leave a Comment »

Mechanistic Insights on forming Cyclopentenones

Posted by naturalproductman on March 22, 2011

Stephen Caddick at the University College of London and Carlos Afonso and co-workers at CQFM in Portugal have reported in Tetrahedron on an interesting ring opening and closing of a pyranone to form a cyclopentenone.  DFT calculations were used to determine the mechanism.

pyranone

Tetrahedron paper

Posted in Cascade Reactions, Computational, Mechanistic, Methodology, Organocatalytic | Leave a Comment »

1-2-1 Type Cascade Reaction

Posted by naturalproductman on March 22, 2011

Cyclize then couple then cyclize again – this cascade reaction was presented by Keisuke Kato and co-workers at Toho University in ACIEE.

cyclize

ACIEE paper

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

Alopecuridine Synthesis

Posted by naturalproductman on March 22, 2011

Yong-Qiang Tu and co-workers at Lanzhou University have reported in ACIEE on the total synthesis of alopecuridine.  The five membered ring was accessed via a SmI2 mediated pinacol coupling.

alopecuridine

ACIEE paper

Posted in Alkaloids, Cascade Reactions, Methodology, Named Reactions, Pinacol coupling, Pinacol rearrangement, Ring forming | Leave a Comment »

Palladium’s C-C Cleavage

Posted by naturalproductman on March 21, 2011

Christopher Douglas and co-workers at the University of Minnesota have reported in Organic Letters on a palladium catalyzed C-C bond dissociation cascade.

C-C activation

 

OL paper

Posted in C-C Bond Breaking, Methodology, Palladium, Transition Metal | Leave a Comment »