Archive for the ‘Mechanistic’ Category
Posted by naturalproductman on November 24, 2015
Posted by naturalproductman on October 16, 2015
Leadlay (University of Cambridge) and Sun (Wuhan University) and co-workers have reported in Chemical Science on thiotetronate biosynthesis.
Posted by naturalproductman on October 5, 2015
David Collum and colleague have reported in JACS on the solution structure of an Evans enolate.
Posted by naturalproductman on October 1, 2015
Kendall Houk and co-workers reported in JACS on a mechanistic investigation on a reaction discovered by Tius: the asymmetric Nazarov cyclization catalyzed by a thiourea-primary amine catalyst.
Posted by naturalproductman on September 25, 2015
Peter Leadlay and co-workers from the University of Cambridge have reported in ACIE on the enzyme that makes the tetrahydropyran ring in salinomycin. The tetrahydropyran is proposed to come from a diol where one of the hydroxy groups is in the beta-position to a ketone and subsequently dehydrates to form an enone. The enone undergoes an intramolecular Michael reaction to form the tetrahydropyran. However, when the reaction is done in vitro with the purified enzyme, they don’t see the enone intermediate, so I wonder if it is a processive reaction; in other words, the enone forms in the enzyme active site without being released and cyclizes to the tetrahydropyran.
Posted by naturalproductman on September 4, 2015
Miguel Garcia-Garibay and co-workers at UCLA have reported in Organic Letters on a denitrogenation reaction of a triazoline using light to make an aziridine.
Posted by naturalproductman on July 13, 2015
Hafize Ozcan and co-workers from Trakya University in Turkey have reported in Tetrahedron on an interesting mechanistic investigation of the Newman-Kwart reaction.
Posted by naturalproductman on June 9, 2015
Ulrich Koert and co-workers from Philipps-University Marburg have reported in Organic Letters on an alpha-ketol rearrangment.They heat the reaction in a sealed tube to 70 degrees and the solvent is in DCM – with 2.5 mol equivalents of BF3 etherate, sounds a bit harsh – but nonetheless an interesting sigmatropic rearrangement.
Posted by naturalproductman on May 2, 2015
Jeffrey Aube (University of Kansas) and Dean Tantillo (UC Davis) have teamed up to study the mechanism of a domino acylation-Diels Alder reaction.