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Archive for the ‘Named Reactions’ Category

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 »

Fusarisetin A synthesis

Posted by naturalproductman on January 27, 2016

Yandong Zhang and co-workers at Xiamen University have reported in Organic Letters on a synthesis of fusarisetin A using a one pot intramolecular Diels-Alder/Mukaiyama aldol reaction cascade sequence.

OL paper

Posted in Cascade Reactions, Diels-Alder, Named Reactions, One pot, Total Synthesis | Leave a Comment »

From carboxylic acid to ketone

Posted by naturalproductman on January 26, 2016

Peter Schreiner and co-workers from Justus-Liebig University have reported in ACIE on an asymmetric Dakin-West reaction. I am reminded of a similar transformation from carboxylic acid chlorides to trifluoroketones reported by Samir Zard’s group. From my own experience, the Zard reaction also works with just a carboxylic acid as the starting material (except, as pointed out – is not an asymmetric reaction).

 

ACIE paper

Posted in Asymmetric, Cascade Reactions, Dakin-West, Methodology, Named Reactions | 2 Comments »

Hetero-Diels-Alder/Oxy-Michael cascade

Posted by naturalproductman on January 22, 2016

John Gao and co-workers from UT San Antonio have reported in ACIE on the use of modularly designed organocatalysts (MDO) to effect a hetero-Diels-Alder/oxy-Michael cascade reaction.

 

ACIE paper

Posted in Cascade Reactions, Diels-Alder, Kinetic resolution, Methodology, Named Reactions, Organocatalytic, Oxy-Michael | Leave a Comment »

Access to 7-membered rings from lactams

Posted by naturalproductman on January 22, 2016

Scott Sieburth and co-workers from Temple University reported in ACIE on an interesting transformation converting a delta-lactam to a cycloheptanone ring.

 

ACIE paper

Posted in Cascade Reactions, Kulinkovich-de Meijere, Named Reactions, Titanium, Transition Metal | Leave a Comment »

 
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