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Archive for the ‘Methodology’ Category

The Synthesis of 12alpha-Hydroxy Steroids

Posted by naturalproductman on November 3, 2018

Francis Yoshimoto and co-workers at the University of Texas at San Antonio reported in Steroids on the synthesis of 12alpha-hydroxy steroid derivatives to biochemically characterize P450 8B1, the enzyme implicated in cardiovascular health and obesity. Both 7-keto DHEA and 12alpha-hydroxy 7-keto DHEA had antagonistic properties towards the NMDA receptor.

Screen Shot 2018-11-03 at 3.27.25 PM

 

Steroids paper

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Posted in C-H activation, Stereochemistry, Steroids, Total Synthesis | Leave a Comment »

First paper published

Posted by naturalproductman on November 6, 2017

Francis Yoshimoto and co-workers at the University of Texas at San Antonio report in the journal, Steroids, on the synthesis of a neurosteroid produced in the brains, 7alpha-hydroxypregnenolone, through an allylic C7-oxidation reaction. The oxidation was performed through either a C7-oxidation through CrO3 in the presence of 3,5-dimethylpyrazole followed by a stereoselective reduction or a regioselective and stereoselective allylic benzoyloxylation using CuBr and tert-butylperoxy benzoate.

STEROIDS FKY

Steroids paper

Posted in C-H activation, Stereochemistry, Steroids, Total Synthesis | Leave a Comment »

Reversing the epoxidation

Posted by naturalproductman on September 7, 2016

Rongbiao Tong and co-workers from the Hong Kong University of Science and Technology reported in Organic Letters on a copper catalyzed de-epoxidation reaction.

OL paper

Posted in Copper, Methodology | Leave a Comment »

C-H Allylation

Posted by naturalproductman on September 7, 2016

Hon-Wai Lam and co-workers from the University of Nottingham have reported in JACS on a rhodium catalyzed C-H allylation process.

 

JACS paper

Posted in C-H activation, Rhodium | Leave a Comment »

Cope rearrangement

Posted by naturalproductman on August 23, 2016

James Gleason and colleague at McGill University have reported in ACIE on an organocatalytic Cope rearrangement.

 

ACIE paper

Posted in Cascade Reactions, Methodology, Organocatalytic, Sigmatropic Rearrangements | Leave a Comment »

Carbonylative spirolactonization

Posted by naturalproductman on August 22, 2016

Mingji Dai and co-workers reported in JACS on a Pd-catalyzed spirolactonization.

 

JACS paper

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

Spinosyn A synthesis

Posted by naturalproductman on August 22, 2016

Mingji Dai and co-workers at Purdue reported in JACS on the synthesis of spinosyn A through a carbonylative macrolactonization.

 

JACS paper

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

Transamination reaction

Posted by naturalproductman on August 22, 2016

Here’s a transamination reaction reported in JACS. Normally pyridoxal-phosphate containing enzymes do this in nature but this is the biomimetic approach.

 

JACS paper

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

Triiodide-mediated C-H amination

Posted by naturalproductman on July 31, 2016

David Nagib and co-workers from the Ohio State University have reported in ACIE on a triiodide mediated C-H amination reaction.

 

ACIE paper

Posted in C-H activation, Hypervalent Iodine, Methodology | Leave a Comment »

Amidation-C-H activation cascade

Posted by naturalproductman on July 31, 2016

Santhosh Mhaske and colleague at CSIR have reported in Organic Letters on a palladium catalyzed amidation-C-H activation cascade.
OL paper

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