Epoxide‐Opening Cascades in the Synthesis of Polycyclic Polyether Natural Products

Vilotijević, Ivan; Jamison, Timothy F.

doi:10.1002/anie.200900600

Cited by 210 publications

(96 citation statements)

References 299 publications

(392 reference statements)

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“…The synthesis of polyether natural products has provided some classic examples in this regard. [63] A superb example is Corey and coworkers' recent and remarkably short, enantioselective synthesis of (þ)-omaezakianol (Scheme 5). [64a] A five-fold asymmetric epoxidation of chlorohydrin 1 generates penta-epoxide 2, which, upon treatment with camphorsulfonic acid, undergoes a spectacular substratecontrolled five-fold polycyclisation sequence to generate [42] Pronin.…”

Section: One-component Domino Reactionsmentioning

confidence: 99%

Multi-Bond Forming Processes in Efficient Synthesis

Green¹,

Sherburn²

2013

Aust. J. Chem.

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An increasing number of synthetic organic chemists are embracing the philosophy of efficiency. Herein we highlight multi-bond forming processes, which form two or more new covalent bonds in a single synthetic operation. Such processes, which have the ability to rapidly increase structural complexity, are preeminent in contemporary synthetic organic chemistry. In this short review we classify, analyse, and contrast contemporary multi-bond forming processes, frame these cutting edge contributions within a historical context, and speculate on likely future developments in the area.

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Section: One-component Domino Reactionsmentioning

confidence: 99%

Multi-Bond Forming Processes in Efficient Synthesis

Green¹,

Sherburn²

2013

Aust. J. Chem.

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“…Indeed, since Cane-Celmer-Westley's mechanistic proposal for the biosynthesis of polyether ionophores, 10 epoxide opening cascades have become increasingly studied in synthetic organic chemistry as an elegant way to access poly-THF structures. 11 For example, Marshall et al reported a zinc-mediated cascade cyclization of a triepoxide, allowing the access to bis-THF in moderate to good yields (Scheme 1). 12,13 This process allows control of all the stereocenters upstream set by Sharpless and Shi epoxidation reactions and was successfully applied to the synthesis of C17-C32 fragment of Ionomycin.…”

Section: Thf Synthesis By C-o Bond Formation 1 Epoxide Openingmentioning

confidence: 98%

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

et al. 2016

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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.

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“…3b) provide a justified obstacle to proving or disproving this biosynthetic hypothesis. The kinetic preference for epoxide-opening cascades lies in favor of the exo products, instead of the endo moieties of the ladder poly cyclic ethers 39 . Directing epoxide-opening cascades toward the endo products in the laboratory is made more complex by the inclusion of methyl groups at the ring junctions-seen in every member of the family 40 .…”

Section: Overturning Chemical 'Rules'mentioning

confidence: 99%

Lessons and revelations from biomimetic syntheses

2011

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Biomimetic synthesis describes the field of organic chemistry that aims to emulate the natural, biosynthetic processes toward natural products. As well as providing insight into how molecules are formed in nature, the benefits of this approach to total synthesis are numerous and extend beyond the gains typical of traditional synthesis. For example, using biosynthetic proposals to design a synthetic route can highlight alternative methods to the desired target. The pursuit of biomimetic syntheses also promotes the development of new reactions to prove or disprove a biosynthetic proposal or to unravel mechanistic implications of a proposed biosynthesis and can lead to the identification of new natural products. Here we look at some recent compelling examples and examine how biomimetic synthesis has led to the discovery of new procedures and principles that would not have been found by other approaches.

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Epoxide‐Opening Cascades in the Synthesis of Polycyclic Polyether Natural Products

Cited by 210 publications

References 299 publications

Multi-Bond Forming Processes in Efficient Synthesis

Multi-Bond Forming Processes in Efficient Synthesis

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

Lessons and revelations from biomimetic syntheses

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