Naturalproductman’s Blog

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Archive for the ‘Methodology’ Category

Rearrange to more complexity

Posted by naturalproductman on July 27, 2014

Paul Hergenrother and co-workers from UIUC have reported in ACIE on an interesting rearrangement to form fenestrane ring systems.

cyclopropane

ACIE paper

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

Electrocyclic ring opening to ketonitrones

Posted by naturalproductman on July 27, 2014

Masahiro Terada and co-workers from Tohoku University have reported in Organic Letters on a copper-catalyzed rearrangement to form alpha,beta-unsaturated ketonitrones.

nitrone

OL paper

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

Aryl halide couplings with Sp3-carbons

Posted by naturalproductman on July 27, 2014

Gary Molander and colleagues reported in Science on a photoredox nickel dual catalysis for a cross coupling reaction between an sp3-hybridized organoboron and an aryl halide.

Science paper (Molander)

In the same issue, David Macmillan and co-workers have reported on a photoredox reaction involving a nickel catalyzed coupling between an sp3-alpha-carboxyl and an aryl halide.

Science paper (Macmillan)

 

Posted in Cascade Reactions, cross coupling, Light Mediated, Methodology, Nickel, Transition Metal | Leave a Comment »

C-O bond cleavage with Ir

Posted by naturalproductman on July 27, 2014

Alan Goldman and co-workers from Rutgers have reported in ACIE on an iridium pincer complex catalyzed C-O bond cleavage.

C-O

ACIE paper

Posted in Catalytic, Iridium, Methodology, Transition Metal | Leave a Comment »

Bislactone desymmetrization

Posted by naturalproductman on July 27, 2014

Jieping Zhu and co-workers have reported in ACIE on the synthesis of rhazinilam and leucomidine B.

desymmetrize

ACIE paper

Posted in Alkaloids, Asymmetric, C2-Symmetric, Cascade Reactions, Methodology, Organocatalytic | Leave a Comment »

Aluminum porphyrin

Posted by naturalproductman on July 27, 2014

George O’Doherty and co-workers from Northeastern University have reported in JACS on an aluminum catalyzed beta-lactone synthesis from epoxides.

aluminum

JACS paper

Posted in Cascade Reactions, Lactones, Methodology, Total Synthesis | Leave a Comment »

Carboboration, organocatalytically

Posted by naturalproductman on July 27, 2014

Masaya Sawamura and co-workers at Hokkaido University have reported in JACS on a carboboration of alkynoates.

carboboration

JACS paper

Posted in Conjugate Additions, Methodology, Organocatalytic | Leave a Comment »

Rhodium cascade

Posted by naturalproductman on July 16, 2014

Richmond Sarpong and co-workers have reported in ACIE on a rhodium catalyzed cascade reaction involving an aza-Cope rearrangement.

Cope

ACIE paper

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

Claisen-Diels-Alder cascade to spirooliganones A and B

Posted by naturalproductman on July 16, 2014

Rongbiao Tong and co-workers from the Hong Kong University of Science and Technology have reported in Org Lett on a slick reaction to form spirooliganones.

 
spirooliganones

OL paper

Posted in Cascade Reactions, Claisen rearrangement, Diels-Alder, Methodology, Named Reactions, Total Synthesis | Leave a Comment »

Indole alkaloid synthesis

Posted by naturalproductman on July 15, 2014

Corey Stephenson and colleague at the University of Michigan have reported in JACS on the synthesis of pseudotabersonine. A mental roadblock for me was when I was looking at the paper, I was trying to find the structure of catalyst 5, which was the iridium catalyst used for a ring opening reaction, but just found the number 5 in the scheme. Within the text of the paper however it says Ir(dF(CF3)ppy)2(dtbbpy)PF6, which was cited with a Sigma Aldrich catalog number.

 

photoredox

JACS paper

Posted in Alkaloids, Indoles, Iridium, Light Mediated, Methodology, Transition Metal | Leave a Comment »

 
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