Naturalproductman’s Blog

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Archive for the ‘Ring Opening’ Category

Asymmetric metathesis

Posted by naturalproductman on September 8, 2014

Grubbs and colleagues have reported in JACS on their studies with asymmetric ring closing metathesis.

asymmetric

JACS paper

Posted in Asymmetric, Cascade Reactions, Metathesis, Methodology, Ring Opening | 1 Comment »

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 »

Cyclopropanol ring opening

Posted by naturalproductman on August 22, 2012

Jin Kun Cha and co-workers at Wayne State University have reported in ACIE on a ring opening of cyclopropanol using stoichiometric diethyl zinc.

sn2 prime

ACIE paper

Posted in Cascade Reactions, Methodology, Ring Opening, Sn2 prime, Transition Metal, Zinc | Leave a Comment »

Furan ring opening

Posted by naturalproductman on May 2, 2012

Alexander Butin and co-workers at  Kuban State Technological University in the Russian Federation have reported in Tetrahedron on a tin mediated furan ring opening reaction.

furan

Tetrahedron paper

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

Rumphellaone A synthesis

Posted by naturalproductman on January 11, 2012

Shigefumi Kuwahara and co-workers from Tohoku University have reported in Tetrahedron Letters on the synthesis of rumphellaone A.  They accessed the four membered ring from a base promoted intramolecular epoxide ring opening.

cyclobutane

TL paper

Posted in Cascade Reactions, Lactones, Methodology, Ring forming, Ring Opening | Leave a Comment »

Aplyronine A progress

Posted by naturalproductman on December 5, 2011

Philip Fuchs and co-workers at Purdue University have reported in Organic Letters on their progress towards aplyronine A.  They used a seven membered ring with four stereocenters as a precursor to the C1-C20 fragment.

seven

OL paper

Posted in Methodology, Polyketides, Ring Opening | 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 »

NHC catalysis

Posted by naturalproductman on October 23, 2011

David Lupton and co-worker from Monash University have reported in Chemical Science on a carbene catalyzed cyclopropane-rearranging/C-C bond forming cascade.

cyclopropane

Chemical Science paper

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

Regioselective epoxide opening

Posted by naturalproductman on October 23, 2011

Pilar López-Ram-de-Víu and co-workers have reported in Organic and Biomolecular Chemistry on an epoxide opening reaction using a Grignard reagent – and the regioselectivity is switched when they use it in the presence of copper bromide.

epoxide

OBC paper

Posted in Copper, Grignard, Methodology, Named Reactions, Named Reagents, Regioselective, Ring Opening, Transition Metal | Leave a Comment »

 
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