Biomimetic iterative method for polyketide synthesis
An iterative method for synthesizing polyketides was demonstrated, in which the chain elongation of a carboxylic acid was performed by decarboxylative dehydration condensation with a malonic acid half thioester. After transforming the resulting β-ketothioester into an appropriate form, the carboxylic acid functionality was regenerated for the next elongation step.
Akagawa, Kengo,Kudo, Kazuaki
supporting information
p. 8645 - 8648
(2017/08/10)
Tandem cross-metathesis/hydrogenation/cyclization reactions by using compatible catalysts
(Matrix presented) A one-pot tandem cross-metathesis/hydrogenation/cyclization procedure was achieved at room temperature, under 1 atm of hydrogen, in the presence of a ruthenium catalyst and PtO2 showing the compatibility of the two catalysts. This tandem reaction allows the synthesis of substituted lactones and lactols from acrylic acid and acrolein, respectively, in the presence of unsaturated alcohols.
Cossy, Janine,Bargiggia, Frederic,BouzBouz, Samir
p. 459 - 462
(2007/10/03)
3,4-Dehydro-2-hydroxy-6-(2-phenethyl)tetrahydropyran. 1,3-Acyclic diastereoselection in reaction with MeOH and its application in the synthesis of a racemic mevinolin analog
3,4-Dehydro-2-hydroxy-6-(2-phenethyl)tetrahydropyran (6) and its dimer (7) both react with MeOH in the presence of a catalytic amount of conc. HCl to provide 2,4-bismethoxy-6-(2-phenylethyl)tetra-hydropyran with a decent level of 1,3-acyclic diastereoselection in favour of the 4,6-trans derivative (9a). The ratio of the arabino (9a) and xylo (9b) structures was an unprecedented 4:1. Models to account for the observed diastereoselectivity are discussed. Further transformation to the 2-oxo derivative and unmasking of the 4-OH function provide a rapid entry into a racemic mevinolin analog (14).
Yadav, Veejendra K.,Kapoor, Kamal K.
p. 8 - 13
(2007/10/03)
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