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Archive for the ‘Ring expansion’ Category

This transformation involves making the ring bigger.

Oxepanes via Ferrier

Posted by naturalproductman on August 31, 2014

Srinivasan Chandrasekaran and co-workers at the Indian Institute of Science have reported in Tetrahedron on a Ferrier rearrangement to form oxepanes.

 

Ferrier

Tetrahedron paper

Posted in Cascade Reactions, Ferrier, Methodology, Named Reactions, Ring expansion, Ring Opening | Leave a Comment »

Cyclobutenone ring expansion

Posted by naturalproductman on August 20, 2014

Guangbin Dong and colleague at UT Austin have reported in ACIE on the synthesis of cycloinumakiol through a rhodium catalyzed cascade reaction that forms the tetracyclic ring structure of the compound.

C-C

ACIE paper

Posted in Methodology, One pot, Rhodium, Ring expansion, Ring forming, Ring Opening, Total Synthesis, Transition Metal | Leave a Comment »

C-H arylation of cyclopropanes

Posted by naturalproductman on November 19, 2012

Nicolai Cramer and co-worker from ETH Zurich have reported in ACIE on a C-H arylation of cyclopropanes.

cyclopropane

ACIE paper

Posted in C-H activation, Methodology, Palladium, Ring expansion, Transition Metal | Leave a Comment »

Steroid rearrangement

Posted by naturalproductman on July 9, 2012

Hans Gunther-Schmalz and colleagues have reported in Organic Letters on a BF3-promoted rearrangement of a steroid backbone.

ring

OL paper

Posted in Cascade Reactions, Mechanistic, Methodology, Ring expansion, Seven-Membered Rings | Leave a Comment »

Mersicarpine synthesis

Posted by naturalproductman on April 20, 2012

Hidetoshi Tokuyama and co-workers from the University of Toyama have reported in Organic Letters on their synthesis of mersicarpine.

mersicarpine

OL paper

Posted in Alkaloids, Methodology, Ring expansion | Leave a Comment »

C-C bond cleavage via SnCl4

Posted by naturalproductman on December 2, 2011

Matthias Brewer and co-workers at the University of Vermont have reported in Organic Letters on a tin promoted C-C bond cleavage.

carbene

OL paper

Posted in C-C Bond Breaking, Cascade Reactions, Methodology, Ring expansion, Ring Opening | Leave a Comment »

Trigonoliimine progress

Posted by naturalproductman on October 12, 2011

Yian Shi and co-workers have reported in Organic Letters on their progress towards trigonoliimines using an anion cascade to form the seven membered ring.

trigonoliimines

OL paper

Posted in Alkaloids, Cascade Reactions, Methodology, Ring expansion, Ring forming, Seven-Membered Rings | Leave a Comment »

Reaction after another

Posted by naturalproductman on September 25, 2011

Corey Stephenson and colleague at Boston University have reported in Organic Letters on an iridium catalyzed tandem reaction using visible light – the reaction forms a divinyl cyclopropane intermediate that undergoes a Cope rearrangement.

cascade

OL paper

Posted in Cascade Reactions, Cope rearrangement, Iridium, Methodology, Named Reactions, Ring expansion, Ring forming, Transition Metal | Leave a Comment »

Desymmetrize this

Posted by naturalproductman on May 23, 2011

Keiji Maruoka and co-workers from Kyoto University have reported in JACS on a desymmetrization process of a cyclohexanone using an alphadiazoacetate reagent to afford seven membered rings.

binol

JACS paper

Posted in Asymmetric, Carbene, Cascade Reactions, Desymmetrization, Methodology, Ring expansion, Ring Opening | Leave a Comment »

Rippertenol synthesis

Posted by naturalproductman on May 17, 2011

Scott Snyder and co-workers have reported in JACS on their synthesis of rippertenol.

rippertenol

JACS paper

Posted in Aldol, Diels-Alder, Methodology, Named Reactions, Ring expansion, Sesquiterpenoids, Seven-Membered Rings, Total Synthesis | Leave a Comment »

 
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