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Archive for the ‘Cascade Reactions’ Category

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

Trichodermamides A, B, and C syntheses

Posted by naturalproductman on June 30, 2015

Oleg Larionov and co-workers at UT San Antonio have reported in JACS on the syntheses of trichodermamides A, B, and C.

polyketide

JACS paper

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

α-Ketol rearrangement

Posted by naturalproductman on June 9, 2015

Ulrich Koert and co-workers from Philipps-University Marburg have reported in Organic Letters on an alpha-ketol rearrangment.They heat the reaction in a sealed tube to 70 degrees and the solvent is in DCM – with 2.5 mol equivalents of BF3 etherate, sounds a bit harsh – but nonetheless an interesting sigmatropic rearrangement.

 
ketol
OL paper

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

Sn2 prime with trichloroacetimidates

Posted by naturalproductman on May 28, 2015

At first look of the abstract figure I thought this was an Overman rearrangement paper but no, trichloroacetimidates are also good leaving groups for Sn2 prime reactions.

Sn2 prime

ACIE paper

Posted in Cascade Reactions, Methodology, Ring forming, Sn2 prime | Leave a Comment »

Synthesis of Paclitaxel exploiting new ways

Posted by naturalproductman on May 28, 2015

Noritaka Chida and co-workers from Keio University have reported in Organic Letters on a radical cyclization approach toward taxol.

taxol

OL paper

They access the oxetane ring via intramolecular mesylate displacement.

OL paper2

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

Brevisin via epoxide ring opening

Posted by naturalproductman on May 28, 2015

Timothy Jamison and co-workers have reported in JACS on their formal synthesis of brevisin.

polyepoxide

JACS paper

Posted in Cascade Reactions, Formal Synthesis, Rhodium, Total Synthesis, Transition Metal | Leave a Comment »

Methylene transfer

Posted by naturalproductman on May 2, 2015

Itaru Nakamura and co-workers from Tohoku University have reported in ACIE on a gold catalyzed methylene transfer sequence to access isoxazolines.

methylene

ACIE paper

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

Reverse Claisen cascade

Posted by naturalproductman on April 16, 2015

Yongjia Shang and co-workers from Anhui Normal University have reported in JOC on an interesting iron catalyzed cascade reaction.

JOC paper

Posted in Cascade Reactions, Claisen rearrangement, Iron, Methodology, Sigmatropic Rearrangements, Transition Metal | Leave a Comment »

Pd-catalyzed DKR

Posted by naturalproductman on April 16, 2015

Xinjun Luan and co-workers have reported in JACS on a palladium catalyzed dynamic kinetic resolution of biaryls to spirocyclic centers.

spirocycle

JACS paper

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

A Formal Metathesis

Posted by naturalproductman on April 16, 2015

Zhang Jie-Shi and co-workers from the Chinese Academy of Sciences have reported in JACS on a rhodium catalyzed exchange between an aryl keton and an aryl carboxylic acid to form aliphatic carboxylic acids and biaryl compounds.

cascade

JACS paper

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

Triyne benzannulation

Posted by naturalproductman on April 16, 2015

Daesung Lee and co-workers have reported in ACIE on a benzannulation of triynes.

benzannulation

ACIE paper

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

 
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