Naturalproductman’s Blog

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Archive for October, 2010

Cyclizations of 1,5-Enynes with no Metal

Posted by naturalproductman on October 30, 2010

Veronique Michelet and co-workers from UMR in Paris have published in Organic Letters on cyclization reactions of 1,5-enynes using NIS.

cyclization

 

OL paper

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

Dihypoestoxide Synthesis

Posted by naturalproductman on October 30, 2010

Christopher Hayes and co-workers from the University of Nottingham have published in Organic Letters on their progress towards dihypoestoxide.  This molecule if you look closely is a dimer, which can be disconnected to two enone fragments that underwent a hetero-Diels Alder reaction.

dihypoestoxide

OL paper

Posted in Cascade Reactions, Cycloaddition, Diels-Alder, Dimer, Methodology, Named Reactions, Pericyclic reactions, Ring forming | Leave a Comment »

Copper-Catalyzed O-H Insertion

Posted by naturalproductman on October 30, 2010

Qi-Lin Zhou and co-workers from Nankai University have published in JACS on a copper catalyzed asymmetric O-H insertion reaction.

copper

 

JACS paper

Posted in C2-Symmetric, Carbene, Cascade Reactions, Copper, Methodology, Ring forming, Transition Metal | Leave a Comment »

Ir-Catalyzed Cyclopropenation

Posted by naturalproductman on October 30, 2010

Tsutomu Katsuki and co-workers from Kyushu University have published in JACS on a cyclopropene synthesis from an alkyne.

cyclopropene

JACS paper

Posted in Asymmetric, Iridium, Methodology, Transition Metal | Leave a Comment »

Didemnaketal Synthesis

Posted by naturalproductman on October 29, 2010

Haruhiko Fuwa and co-workers from Tohoku University have published in Organic Letters on a synthesis of didemnaketal which has an IC50 value of 1 micromolar against HIV-1 protease.  The spiroketal unit was accessed from a PPTS catalyzed condensation of an alcohol and a dihydropyran.

spiroketal

 

OL paper

Posted in Cascade Reactions, cross coupling, Diseases, HIV, Methodology, Palladium, Polyketides, Spiroketals, Suzuki-Miyaura, Transition Metal | Leave a Comment »

Sn2 with Aldehyde Nucleophiles

Posted by naturalproductman on October 29, 2010

Dhar Yadav and co-workers from the University of Allahabad have published in Synlett on an N-heterocyclic carbene catalyzed coupling between an allylic bromide and an aldehyde.

bromide

Synlett paper

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

Rameswaralide Core

Posted by naturalproductman on October 28, 2010

Barry Trost and co-workers have published in Tetrahedron Letters on the synthesis of the core of rameswaralide.

seven

TL paper

Posted in Cascade Reactions, Methodology, Ring forming, Ring Opening, Ruthenium, Seven-Membered Rings, Transition Metal | Leave a Comment »

Ene Reaction with Palladium

Posted by naturalproductman on October 28, 2010

Masanari Kimura and co-workers from Nagasaki University have published in JACS on a palladium catalyzed reaction that basically adds an allyl group onto an aldehyde.  The mechanism involves an oxapalladacyclopentane intermediate.

palladium

 

JACS paper

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

Hydroacylation with Rh

Posted by naturalproductman on October 28, 2010

Vy Dong and co-workers at the University of Toronto have published in JACS on a rhodium catalyzed hydroacylation where they make a meso cyclopropene compound into a chiral molecule using a Josiphos ligand.

JOSIPHOS

 

JACS paper

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

Palladium Catalyzed C-H Activation through H-Bonds

Posted by naturalproductman on October 28, 2010

Jianliang Xiao and co-workers from the University of Liverpool have published in JACS on a hydrogen bonding promoted C-H activation process.

hydrogen bonding

 

JACS paper

Posted in C-H activation, Cascade Reactions, cross coupling, Methodology, Palladium, Transition Metal | Leave a Comment »

 
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