Potent oligomerization and macrocyclization activity of the thioesterase domain of vicenistatin polyketide synthase
The thioesterase domain of the polyketide synthase involved in the biosynthesis of the 20-membered macrolactam antibiotic vicenistatin (VinTE) was found to catalyze oligomerization and macrocyclization of ω-hydroxy fatty acid ethyl esters to afford 17-28-membered macrocyclic lactones. The ring sizes of the macrocycles appear to be limited to the more moderate sizes because of the space limitation of the active site of VinTE. It was also verified that the initially formed linear dimer is first released from the active site of VinTE and then is recognized again by VinTE prior to its transformation to the cyclic dimer.
SYNTHESIS OF PHEROMONES AND RELATED MATERIALS VIA OLEFIN METATHESIS
Methods for preparation of olefins, including 8- and 11-unsaturated monoenes and polyenes, via transition metathesis-based synthetic routes are described. Metathesis reactions in the methods are catalyzed by transition metal catalysts including tungsten-, molybdenum-, and ruthenium-based catalysts. The olefins include insect pheromones useful in a number of agricultural applications.
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Paragraph 0110; 0230
(2018/09/12)
Mild method for the selective esterification of carboxylic acids based on the Garegg-samuelsson reaction
A mild method for the selective esterification of primary alcohols is described. The use of different phosphines, I2, and imidazole allows the selective esterification of a wide variety of acids with excellent results. The generation of a bulky phosphonium-carboxylate salt as intermediate could justify the selectivity observed in this process. Additionally, amides also can be synthesized with use of this method.
Morcillo, Sara P.,Alvarez De Cienfuegos, Luis,Mota, Antonio J.,Justicia, Jose,Robles, Rafael
supporting information; experimental part
p. 2277 - 2281
(2011/05/19)
Construction of carbo- And heterocycles using radical relay cyclizations initiated by alkoxy radicals
An efficient method for the rapid construction of carbo- and heterocycles has been developed using radical relay cyclizations initiated by alkoxy radicals. Linear substrates were cyclized to form a wide range of cyclopentane, pyrrolidine, tetrahydropyran, and tetrahydrofuran derivatives in excellent yields. This methodology was utilized as a key step in the synthesis of the tetrahydrofuran fragment in (-)-amphidino-lide K.
Zhu, Hai,Wickenden, Jason G.,Campbell, Natalie E.,Leung, Joe C. T.,Johnson, Kayli M.,Sammis, Glenn M.
supporting information; experimental part
p. 2019 - 2022
(2009/09/08)
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