Naturalproductman’s Blog

Hey, is that a natural product?!

Archive for the ‘Cascade Reactions’ Category

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

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

Advertisements

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 »

[4+2] with diazo esters

Posted by naturalproductman on February 8, 2016

Michael Doyle and co-workers at UT San Antonio have reported in JACS on the first Diels-Alder example involving a diazoester dienophile.

DOYLE jacs 2016

JACS paper

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

Jungermannenones B and C synthesis

Posted by naturalproductman on January 29, 2016

Xiaoguang Lei and co-workers from Peking University have reported in ACIE on the synthesis of jungermannenones B and C.

 

ACIE paper

Posted in Cascade Reactions, Methodology, Radical Chemistry, 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 »

2 Reagents, 2 mechanisms, same product

Posted by naturalproductman on January 28, 2016

Srinivasan Chandrasekaran and colleague at the Indian Institute of Science have reported in Tetrahedron on a mechanistically interesting transformation involving a geminal aminooxygenation of a vinyl arene. Two different reaction conditions were identified: one with m-CPBA, the other with a hypervalent iodine reagent. The former underwent a deuterium shift on the gem-dideuterated-styrene starting material and the latter does not.

01.28.2016 naturalproductman.gif

Tetrahedron paper

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

Expect the unexpected – allylic alcohols from epoxides

Posted by naturalproductman on January 27, 2016

Margaret Brimble and co-workers from the University of Auckland have reported in Organic Letters on a cobalt-catalyzed conversion of an epoxide to an allylic alcohol using the Corey-Chaykovsky reagent.

 

OL paper

Posted in Cascade Reactions, Cobalt, Methodology, Transition Metal | 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 »