Naturalproductman’s Blog

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Archive for the ‘Light Mediated’ Category

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 »

Asymmetric [2+2]

Posted by naturalproductman on April 25, 2014

Tehshik Yoon and co-workers published in Science on an enantioselective [2+2] reaction.

Science paper

Posted in Asymmetric, Cycloaddition, Light Mediated, Methodology, Pericyclic reactions, [2+2] | Leave a Comment »

17-Deoxyprovidencin synthesis

Posted by naturalproductman on March 7, 2014

Johann Mulzer and co-workers have reported in ACIE on the synthesis of 17-deoxyprovidencin.

17-deoxyprovidencin
ACIE paper

Posted in Asymmetric, Light Mediated, Methodology, Total Synthesis | Leave a Comment »

Light mediated rearrangement of natural products

Posted by naturalproductman on November 12, 2012

Yoshito Kishi and co-workers have published in JACS on the photochemistry of mycolactone A and B.

light

JACS paper

Similarly Hong-Xiang Lou and co-workers at Shandong University have published in JACS on the light induced interconversion of pallambins.

pallambins

OL paper

Posted in Light Mediated, Methodology, Polyenes | Leave a Comment »

Ullman with light

Posted by naturalproductman on November 2, 2012

I guess Greg Fu made a statement at Caltech with his Science paper in collaboration with the Jonas Peters group. This Science paper discloses an Ullman reaction (copper mediated aryl iodide and amine coupling) in the presence of light.

 

Science paper

Posted in Copper, cross coupling, Light Mediated, Methodology, Transition Metal, Ullmann | Leave a Comment »

Acutimine approach

Posted by naturalproductman on August 15, 2012

Sarah Reisman and colleague have reported in Organic Letters on their elegant approach to acutimine via a [2+2] cycloaddition – however, their retro-aldol reaction to open the cyclobutane ring failed.

acutimine

OL paper

Posted in Alkaloids, Cycloaddition, Light Mediated, Methodology, Pericyclic reactions, [2+2] | Leave a Comment »

Ring size matters

Posted by naturalproductman on August 6, 2012

Petr Klan (Masaryk University) and Richard Givens (University of Kansas) have reported in JOC on a study of the photo-Favorskii rearrangement.

ring size

JOC paper

Posted in Cascade Reactions, Favorskii rearrangement, Light Mediated, Methodology, Named Reactions, Ring contraction | Leave a Comment »

Eliptifoline and ponapensin syntheses

Posted by naturalproductman on July 31, 2012

John Porco and co-workers have reported in JACS on the synthesis of eliptifoline and ponapensin.

photo

JACS paper

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

Chromium cascade

Posted by naturalproductman on May 8, 2012

Nobuhara Iwasawa and co-workers at Tokyo Institute of Technology have reported in ACIE on a chromium catalyzed cascade.

chromium

ACIE paper

Posted in Cascade Reactions, Chromium, Electrocyclization, Light Mediated, Methodology, Transition Metal | Leave a Comment »

[2+2+2] for endoperoxides

Posted by naturalproductman on February 29, 2012

Tehshik Yoon and co-workers at the University of Wisconsin have reported in Organic Letters on a [2+2+2] cyclization approach to form endoperoxides using oxygen (ie:  O2).

O2

OL paper

Posted in Cascade Reactions, Light Mediated, Methodology, Peroxides, Ruthenium, Transition Metal | Leave a Comment »

 
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