Recent advances in the synthesis of tetrahydrofurans and applications in total synthesis

Abstract

Mousseron. His research interests include the total synthesis of oxygenated cyclic and non cyclic metabolites of polyunsaturated fatty acids, mainly leukotrienes, iso-, phyto-and neuroprostanes, as well as dihydroxylated PUFAs and more recently lipophenols and the understanding of the role of such bioactive lipids and lipophenols by developing collaborations with chemists, biochemists, biologists and clinicians across the world. Jean-Marie Galano studied chemistry at Paul Cézanne Université Marseille and obtained his PhD under the supervision of Honoré Monti in 2001. He then moved to the University of Oxford to pursue a postdoctoral fellowship with David H. Hodgson on the development of new methods for the total synthesis of natural products. In October 2005 he joined the CNRS as a Chargé de Recherche at Université of Montpellier. His research focuses on the total synthesis and discovery of new lipid metabolites, and to discover their potential implications in human health. AbstractMany natural products contain tetrahydrofuran (THF) moieties. Those molecules, often biologically active, may be structurally diverse, e.g. cis or trans THF, mono-, di-, tri-or tetrasubstituted on the furan ring. Thus, the construction of THF is of great interest for the community of organic chemists; especially in developing new methodologies, and applying them in the total synthesis of natural products. The aim of this review is to report recent advances in the field of THF synthesis, as well as the application of these methods to the synthesis of bioactive compounds.

A General Approach to Various Five‐ and Six‐Membered gem‐Difluoroheterocycles: Application to the Synthesis of Fluorinated Analogues of Sedamine

“…[7] Therefore fluorinated derivatives play an important role in bioorganic and medicinal chemistry, and the development of novel synthetic methodologies to prepare selectively fluorinated molecules is a very active research area. [8] Much work has been devoted already to selective monofluorination, as well as introduction of CF 3 groups, but more recently the preparation of gem-difluoro derivatives has attracted great interest to synthetic chemists.…”

“…Cyclic ethers (THP and THF rings), represent important synthetic targets owing to their structures and the biological properties of corresponding molecules, including immunosuppressant, antitumor, antiulcer, antiproliferative, antiparasitic, and anti-inflammatory activities. [3][4][5][6][7][8][9] The diospongin B, with anti- The chemistry of thiopyrans has been less investigated than of the analogous pyrans, although some are of common use in organic synthesis. [12] Further, attractive biological activities for molecules having such a scaffold have also been identified, [13] however very few selectively fluorinated analogues have been described to date.…”

“…They play a vital role in the metabolism of living cells and they are present in a wide variety of drugs, natural products, and biologically important compounds , . The five‐ and six‐membered O ‐, S ‐ and N ‐containing heterocycles such as tetrahydrofurans, tetrahydropyrans and their sulfur analogues, as well as pyrrolidines and piperidines, are at the core of numerous bioactive natural products and drugs. Thus, many elegant synthetic methods have been developed toward corresponding heterocycles.…”

“…Cyclic ethers (THP and THF rings), represent important synthetic targets owing to their structures and the biological properties of corresponding molecules, including immunosuppressant, antitumor, antiulcer, antiproliferative, antiparasitic, and anti‐inflammatory activities . The diospongin B, with antiosteoporotic activity, is a representative example of this class of products (Figure ) .…”

An Overview of Saturated Cyclic Ethers: Biological Profiles and Synthetic Strategies

“…Tetrahydrofuran (THF) moieties occur in many natural products with a wide array of bioactivities [85]; it has encouraged the development of a variety of synthetic methods [86,87].…”