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Archive for the ‘Cascade Reactions’ Category

multiple reactions back to back (to back) in one go

Markovnikov addition – terminal alkynes to ketones

Posted by naturalproductman on April 19, 2016

Chao-Jun Li and co-workers from McGill University reported in Organic Letters on a useful transformation that converts a terminal alkyne to a ketone using trifluoroethanol as the solvent and triflic acid.

 

OL paper

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

From a dithiane-vinyl chloride to furan

Posted by naturalproductman on April 19, 2016

Shouchu Tang and co-workers from Lanzhou University have reported in Organic Letters on an interesting transformation that undergoes an allene intermediate.

 

OL paper

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

Cyclobutenes from alkynes and silyl enol ethers

Posted by naturalproductman on April 14, 2016

Xiaoming Feng and co-workers from Sichuan University have reported in ACIE on a Zn-catalyzed [2+2] reaction between alkynones and cyclic silyl enol ethers.

 

ACIE paper

Posted in Asymmetric, Cascade Reactions, Methodology, Transition Metal, Zinc, [2+2] | Leave a Comment »

Cyclopropanation ring expansion

Posted by naturalproductman on April 8, 2016

Martin Trmblay and co-workers from Infinity Pharmaceuticals have reported in Organic Process Research & Development on a scalable 6 to 7 membered ring expansion towards a hedgehog antagonist. When I looked at the structure it reminded me of cyclopamine.

 

ORPD paper

Posted in Cascade Reactions, Methodology, Ring expansion, Zinc | Leave a Comment »

ent-Ascospiroketals A and B syntheses

Posted by naturalproductman on April 7, 2016

Rongbiao Tong and colleague from Hong Kong University of Science and Technology have reported in Organic Letters on the synthesis of ascospiroketals A and B.

 

OL paper

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

Rh- and Au- Cooperative Catalysis

Posted by naturalproductman on April 5, 2016

Here’s a neat cascade reaction from Sreenivas Katukojvala and colleague at Indian Institute of Science Education & Research involving the use of rhodium, gold, and diphenylphosphate to access 1,4-oxazines from enaldiazo ketones and N-propargyl anilines.

 

ACIE paper

Posted in Cascade Reactions, Cooperative Catalysis, Gold, Methodology, Rhodium, Transition Metal | Leave a Comment »

Lycopalhine A synthesis

Posted by naturalproductman on March 9, 2016

Fukuyama and Yokoshima and Ochi at Nagoya University  have reported in Organic Letters on the synthesis of lycopalhine A, with the key reaction being a C-N bond formation using a Dess-Martin periodinane oxidation cascade.

fukuyama 2016.gif

OL paper

Posted in Cascade Reactions, Methodology, Total Synthesis | 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 »

Prostaglandin E2 methyl ester synthesis

Posted by naturalproductman on February 15, 2016

Minoru Isobe and co-workers from National Tsing Hua University have reported in JOC on a synthesis of PGE2 methyl ester using a very nice cascade cyclization.

PGE methyl ester Isobe JOC

 

JOC paper

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

 
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