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Archive for the ‘Named Reactions’ Category

Psiguadial B synthesis

Posted by naturalproductman on August 2, 2016

Sarah Reisman and co-workers have reported in JACS on the synthesis of psiguadial B. The key step was a Wolff rearrangement using a Honeywell UV lamp. The supporting information has a nice picture of the reaction set up. It looks like you just shine the lamp next to the reaction flask with aluminum foil around it.

 

JACS paper

Posted in Total Synthesis, Wolff rearrangement | Leave a Comment »

Chiral allenes via Mukaiyama-Aldol

Posted by naturalproductman on July 4, 2016

Benjamin List and co-workers at Max-Planck-Institut für Kohlenforschung reported in ACIE on a Mukaiyama-Aldol approach to access axially chiral allenes.
ACIE paper

Posted in Allenes, Methodology, Mukaiyama, Named Reactions, Organocatalytic | Leave a Comment »

Perforanoid A synthesis

Posted by naturalproductman on May 29, 2016

Xiaojiang Hao and co-workers from the Chinese Academy of Sciences have reported in ACIE on the synthesis of perforanoid A.

 

ACIE paper

Posted in Limonoids, Methodology, Pauson-Khand, Total Synthesis | Leave a Comment »

Mechanism of a Diels-Alderase Enzyme

Posted by naturalproductman on May 7, 2016

Paul Race and co-workers from the University of Bristol have reported in JACS on the details of how an enzyme catalyzes a Diels-Alder reaction using crystal structures and enzyme assays. The enzyme is called spirotetronate cyclase AbyU and is key in forming the macrocyclic structure of abyssomicin C.

 

JACS paper

Posted in Diels-Alder, Enzymes | Leave a Comment »

Hydroxygardnerine, Hydroxygardnutine, Gardnerine, (E)-16-epi-Normacusine B, and Koumine syntheses

Posted by naturalproductman on April 4, 2016

Hiromitsu Takayama and co-workers from Chiba University have reported in Organic Letters on the syntheses of some indole alkaloids using a gold catalyzed 6-exo dig cyclization – which looks like a Conia-ene reaction.

 

OL paper

Posted in Alkaloids, Conia-Ene, Gold, Indoles, Named Reactions, Total Synthesis, Transition Metal | Leave a Comment »

Akaol A synthesis

Posted by naturalproductman on April 4, 2016

Alakesh Bisai and co-workers reported in Organic Letters on a Nazarov approach to akaol A.

 

OL paper

Posted in Named Reactions, Nazarov cyclization, Sesquiterpenes | Leave a Comment »

Some benzyne chemistry

Posted by naturalproductman on February 16, 2016

Michael Greaney and co-workers from the University of Manchester have reported in ACIE on an aryl Truce-Smiles rearrangement to synthesize biaryl amines.

benzyne.gif

ACIE paper

Posted in benzyne, Cascade Reactions, Methodology, Named Reactions, Truce-Smiles rearrangement | Leave a Comment »

[2+2+2] towards rubriflordilactone B

Posted by naturalproductman on February 16, 2016

Zhixiang Xie and co-workers from Lanzhou University have reported in Organic Letters on an approach towards rubriflordilactone B using Wilkinson’s catalyst.

lactone

OL paper

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

Gracilamine formal synthesis

Posted by naturalproductman on February 12, 2016

Scott Snyder and co-workers at the University of Chicago have reported in ACIE on a formal synthesis of gracilamine.

Snyder ACIE 2016.gif

ACIE paper

Posted in Alkaloids, Diels-Alder, Named Reactions, retro-Diels-Alder, Total Synthesis | Leave a Comment »

3 Diels-Alder reactions in 1 go

Posted by naturalproductman on January 29, 2016

Michael Sherburn and co-workers from the Australian National University reported in JOC on a Diels-Alder cascade sequence.

DIELS ALDER CASCADE 01.29.2016.gif

JOC paper

 

Here’s an interesting related ACIE paper by the same group.

Posted in Cascade Reactions, Diels-Alder, Methodology, Named Reactions | Leave a Comment »