Naturalproductman’s Blog

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Archive for August, 2012

Another Nazarov? Or not.

Posted by naturalproductman on August 31, 2012

Zhang-Jie Shi and co-workers at Peking University have reported in Organic Letters on a palladium catalyzed cyclization process, which at first glance looked like it may be a Nazarov reaction but they proved that it probably is not a Nazarov reaction because of the observed kinetic isotope effect when they replaced the aryl hydrogens with deuteriums.

no not a Nazarov

OL paper

Posted in Cascade Reactions, Electrocyclization, Methodology, Named Reactions, Nazarov cyclization, Palladium, Pericyclic reactions, Transition Metal | Leave a Comment »

Acortatarins A and B syntheses

Posted by naturalproductman on August 31, 2012

Derek Tan and co-workers at Sloan Kettering have reported in Organic Letters on their syntheses of acortatarins A and B.

acortatarins A and B

OL paper

Posted in Alkaloids, Methodology, Polyketides, Spiroketals, Total Synthesis | Leave a Comment »

Syntheses through cascade dimerization

Posted by naturalproductman on August 30, 2012

Andrew Lawrence and co-workers at Australian National University have reported in Organic Letters on the syntheses of some polycyclic natural products, incarviditone and incarvilleatone.

racemic

OL paper

Posted in Dimer, Methodology, Total Synthesis | 2 Comments »

Jiadifenin synthesis

Posted by naturalproductman on August 29, 2012

Hongbin Zhai and co-workers at SIOC have reported in ACIE on the synthesis of jiadifenin.  The key [2+2] installed the methyl ester substituent.

jiadifenin synthesis

ACIE paper

Posted in Allenes, Cycloaddition, Methodology, Pericyclic reactions, Total Synthesis, [2+2] | Leave a Comment »

Englerin synthesis

Posted by naturalproductman on August 28, 2012

Susumi Hatakeyama and co-workers at Nagasaki University have reported in JOC on the synthesis of englerin.

englerin

JOC paper

Posted in Asymmetric, Methodology, Sesquiterpenoids | Leave a Comment »

Callipeltoside synthesis

Posted by naturalproductman on August 23, 2012

Steven Ley and co-workers have reported in ACIE on the synthesis of callipeltoside.

macrolide

ACIE paper

Posted in Macrolides, Methodology, Named Reactions, Yamaguchi macrolactonization | Leave a Comment »

Presilphiperfolan-1-ol synthesis

Posted by naturalproductman on August 23, 2012

Stoltz and colleague have reported in ACIE on the enantioselective syntheses of some sesquiterpenoid biosynthetic precursors.  The 5,6-ring system was made from an intramolecular Diels-Alder.

biosynthetic

ACIE paper

Posted in Asymmetric, Cycloaddition, Diels-Alder, Methodology, Named Reactions, Pericyclic reactions, Sesquiterpenoids, Total Synthesis | Leave a Comment »

Cyclopropanol ring opening

Posted by naturalproductman on August 22, 2012

Jin Kun Cha and co-workers at Wayne State University have reported in ACIE on a ring opening of cyclopropanol using stoichiometric diethyl zinc.

sn2 prime

ACIE paper

Posted in Cascade Reactions, Methodology, Ring Opening, Sn2 prime, Transition Metal, Zinc | Leave a Comment »

Selective C-H activation process

Posted by naturalproductman on August 21, 2012

Konstantin Bryliakov and co-workers at the Boreskov Institute of Catalysis in Russia have reported in Organic Letters on a selective C-H activation process.

C-H

OL paper

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

Double benzylic rearrangement

Posted by naturalproductman on August 16, 2012

Angel Montana and co-workers at the University of Barcelona have reported in Tetrahedron on a double benzylic rearrangement.

benzylic

Tetrahedron paper

Posted in Cascade Reactions, Curtin rearrangement, Mechanistic, Methodology, Named Reactions, Sigmatropic Rearrangements | Leave a Comment »

 
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