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Archive for the ‘Pinacol rearrangement’ Category

Posted by naturalproductman on April 20, 2012

Richard Grainger and co-workers at the University of Southampton have reported in Organic Letters on a semipinacol rearrangement of a diol promoted by triphenylphosphine.
semipinacol

OL paper

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

Oxidative Prins-pinacol

Posted by naturalproductman on October 19, 2011

Sylvain Canesi and co-workers at Université du Québec à Montréal have reported in JOC on an oxidative Prins-pinacol approach towards platensimycin.

oxidative
JOC paper

Posted in Cascade Reactions, Hypervalent Iodine, Methodology, Named Reactions, Pinacol rearrangement, Prins | Leave a Comment »

Aspergillin PZ synthesis

Posted by naturalproductman on October 5, 2011

Larry Overman and co-workers have reported in Tetrahedron on the synthesis of aspergillin PZ using a tin mediated Prins-pinacol reaction.

prins

Tetrahedron paper

Posted in Cascade Reactions, Methodology, Named Reactions, Pinacol rearrangement, Prins, Seven-Membered Rings, Total Synthesis | Leave a Comment »

Cinchona-alkaloid promoted cascade

Posted by naturalproductman on May 12, 2011

Yong-Qiang Tu and co-workers at Lanzhou University have reported in Organic Letters on a cinchona alkaloid promoted halogenation/semi-Pinacol rearrangement to form beta-halo ketones asymmetrically.

cinchona

JACS paper

Posted in Alkaloids, Cascade Reactions, Methodology, Named Reactions, Organocatalytic, Pinacol rearrangement | Leave a Comment »

Alopecuridine Synthesis

Posted by naturalproductman on March 22, 2011

Yong-Qiang Tu and co-workers at Lanzhou University have reported in ACIEE on the total synthesis of alopecuridine.  The five membered ring was accessed via a SmI2 mediated pinacol coupling.

alopecuridine

ACIEE paper

Posted in Alkaloids, Cascade Reactions, Methodology, Named Reactions, Pinacol coupling, Pinacol rearrangement, Ring forming | Leave a Comment »

Seragakinone Synthesis

Posted by naturalproductman on February 6, 2011

Keisuke Suzuki and co-workers at the Tokyo Institute of Technology have published in ACIEE on a synthesis of seragakinone – the key steps involve two benzoin cyclizations catalyzed by an N-heterocyclic carbene.

seragakinone

ACIEE paper

Posted in Benzoin condensation, Carbene, Cascade Reactions, Methodology, Named Reactions, Organocatalytic, Pinacol rearrangement | Leave a Comment »

Asymmetric Pinacol Rearrangement

Posted by naturalproductman on November 17, 2010

Jon Antilla and co-workers have reported in ACIEE on a Bronstead-acid catalyzed asymmetric pinacol rearrangement.

bronstead acid


ACIEE paper

Posted in Asymmetric, Methodology, Named Reactions, Organocatalytic, Pinacol rearrangement | Leave a Comment »

Oxidative Prins-Pinacol

Posted by naturalproductman on August 28, 2010

Sylvain Canesi and co-workers have published in Chemistry a European Journal on an oxidative Prins-Pinacol rearrangement to access the 5,6-spirobicyclic portion of platensimycin.

hypervalent iodine

Chemistry – A European Journal paper

Posted in Antibiotics, Cascade Reactions, Hypervalent Iodine, Methodology, Named Reactions, Pinacol rearrangement, Prins, Spirocyclic centers | Leave a Comment »

Liphagal Synthesis

Posted by naturalproductman on April 15, 2010

Jonathan George and co-workers at the University of Oxford have recently reported in Organic Letters on the synthesis of liphagal.  The key step to access the seven membered ring was from a Pinacol type rearrangement of the six membered ring diol using TFA.

liphagal


OL paper

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

 
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