- Macrolactonization Reactions Driven by a Pentafluorobenzoyl Group**
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Macrolactones constitute a privileged class of natural and synthetic products with a broad range of applications in the fine chemicals and pharmaceutical industry. Despite all the progress made towards their synthesis, notably from seco-acids, a macrolactonization promoter system that is effective, selective, flexible, readily available, and, insofar as possible, compatible with manifold functional groups is still lacking. Herein, we describe a strategy that relies on the formation of a mixed anhydride incorporating a pentafluorophenyl group which, due to its high electronic activation enables a convenient access to macrolactones, macrodiolides and esters with a broad versatility. Kinetic studies and DFT computations were performed to rationalize the reactivity of the pentafluorophenyl group in macrolactonization reactions.
- Ciofini, Ilaria,Force, Guillaume,Leb?uf, David,Mayer, Robert J.,Perfetto, Anna
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supporting information
p. 19843 - 19851
(2021/08/13)
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- METHOD FOR THE MANUFACTURE OF OLIGO- AND POLYESTERS FROM A MIXTURE OF CARBOXYLIC ACIDS OBTAINED FROM SUBERIN AND/OR CUTIN AND THE USE THEREOF
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The invention relates to a method for processing mixtures of carboxylic acids obtained as hydrolysis products of suberin and cutin, particularly suberin and cutin isolated from birch bark, to give oligo- and polyesters, or corresponding ester-ethers, as well as the use of the products thus obtained as lubricants, fuel components, plasticizers, surface active agents, environmentally friendly agents for modifying wood, binders in coatings, adhesives, printing inks and composites, further in various cosmetic applications.
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Page/Page column 17-18
(2008/06/13)
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- DEPOLYMERIZATION EXTRACTION OF COMPOUNDS FROM BIRCH BARK
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The invention provides improved processes for the extraction of betulin, lupeol, betulinic acid, suberinic acids, and/or other organic compounds and compositions from birch bark.
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Page/Page column 37; 44
(2008/06/13)
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- Process of preparing ω-hydroxy acids
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A new synthesis of ω-hydroxy acids, which employs commercially available starting materials and lowers the cost of production. The process involves coupling a fatty acyl group by enamine chemistry, followed by a ring expansion and selective reduction of ketoacid.
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- Syntheis of the linoleic acid esters of some unsaturated long-chain ω-hydroxy fatty acids
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The (Z)-32-hydroxy-23-Dotriacontenoic acid ester of linoleic acid (19), a compound implicated in skin metabolism, and related compounds have been synthesized in a nine-steps scheme, starting from 10-undecynoic acid.Overall yield amounted to 5.2percent.
- Heslinga, L.,Pabon, H. J. J.
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p. 348 - 351
(2007/10/02)
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