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Archive for the ‘Mitsunobu’ Category

Mitsunobu with a catalytic twist

Posted by naturalproductman on March 8, 2013

Hiroyuki Ishibashi and co-workers at Kanazawa University have reported in ACIE on a Mitsunobu reaction where they use an iron catalyst and oxygen to regenerate the active azo reagent.

azo

ACIE paper

Posted in Catalytic, Iron, Methodology, Mitsunobu, Named Reactions, Transition Metal | Leave a Comment »

Lysidicin A synthesis from a triple Claisen rearrangement

Posted by naturalproductman on January 17, 2012

Hidenori Watanabe and co-workers at the University of Tokyo have reported in Tetrahedron on the synthesis of lysidicin.  The key reaction being a triple Claisen rearrangement that formed three of the aryl carbon bonds from aryl ether linkages.

Claisen

Tetrahedron paper

Posted in Cascade Reactions, Claisen rearrangement, Methodology, Mitsunobu, Named Reactions, Polyketides, Total Synthesis | Leave a Comment »

Pleurocybellaziridine

Posted by naturalproductman on December 25, 2010

First things first:  Merry Christmas!  Happy holidays!

Toshiyuki Kan and co-workers from the University of Shizuoka have published in ACIEE on the evidence of an aziridine containing amino acid in a fungus called Angel’s wing.  They did some detective work because the aziridine containing amino acid dubbed pleurocybellaziridine is not stable enough for observation.  The carboxylic acid was not stable so they derivitized the natural product to the methyl ester form, which was more stable.  They also synthesized the aziridine containing amino acid to confirm the structures through spectral data.  The aziridine was synthesized via Mitsunobu conditions.  Interestingly the carboxylic acid form is more cytotoxic (87 micromolar, strong activity) compared to the methyl ester (233 micromolar, weak activity).  Pleurocybellaziridine damages the oligodendrocytes, which makes up the myelin sheath in the brain.

angel's wing

ACIEE paper

Posted in Amino Acids, Methodology, Mitsunobu, Named Reactions | Leave a Comment »

Mitsunobu Reaction in an Sn2 Prime Context

Posted by naturalproductman on December 20, 2010

Kazuhiko Sakaguchi and co-workers at Osaka City University have published in Tetrahedron Letters on a Mitsunobu type anti-Sn2 prime reaction.

sn2 prime

 

TL paper

Posted in Cascade Reactions, Mechanistic, Methodology, Mitsunobu, Named Reactions, Sn2 prime | Leave a Comment »

Deguelin Synthesis

Posted by naturalproductman on June 22, 2010

Nicolas Winssinger and co-workers at CNRS have published on the synthesis of deguelin where they utilized a Mitsunobu reaction to combine a homoallylic alcohol and a phenolic ring.

phenol


Chemistry a European Journal paper

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

 
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