Epoxide‐Opening Cascades Triggered by a Nicholas Reaction: Total Synthesis of Teurilene

Rodríguez-López, Julio; Crisóstomo, Fernando Pinacho; Ortega, Nuria; López-Rodríguez, Matías; Martı́n, Victor S.; Martı́n, Tomás

doi:10.1002/anie.201209159

Cited by 42 publications

(18 citation statements)

References 43 publications

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“…27 Toward this end, several acids were tested: BF 3 .Et 2 O resulted in the degradation of the starting compound and gentle Montmorillonite K-10 acid remained inefficient. Finally, the authors observed the desired cyclized product after purification on silica and could therefore carry out the cyclization step using SiO 2 in dichloromethane, followed by deprotection using CAN, which allowed them to complete the synthesis of Teurilene.…”

Section: Scheme 6 : Amberlyst-15 Promoted Cyclization For the Synthesmentioning

confidence: 99%

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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Section: Scheme 6 : Amberlyst-15 Promoted Cyclization For the Synthesmentioning

confidence: 99%

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

et al. 2016

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“…Professor Wiemer has cleverly employed a Lewis acid-catalyzed oxirane cascade involving a phenol en route to schweinfurthin G, while Professor Martin has established that teurilene can be assembled via a triflic acid-catalyzed cascade (Scheme 14) [21,22]. Both cascades proceed in good yields.…”

Section: Oxiranes In Ring-expansion Cascadesmentioning

confidence: 99%

Ring Expansions of Oxiranes and Oxetanes

Smith

Njardarson

2015

Topics in Heterocyclic Chemistry

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This chapter is focused on recently published (2006)(2007)(2008)(2009)(2010)(2011)(2012)(2013)(2014) oxirane and oxetane ring-expansion reactions. The majority of these advances employ oxirane substrates, the discussion of which is broken into five thematic sections representing insertions, cascades, metal-free, metal-catalyzed, and miscellaneous strategies. Oxetane ring-expansion reactions are still rare and are discussed together in one section. A concise graphical summary has been created for every new contribution to this area, highlighting reagents, reaction conditions, scope, mechanistic proposals, and asymmetry where applicable. This review chapter should enable researchers new to the field to quickly assess the current state of the art.

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“…In Figure 2 are the structures of the natural products for which the highlighted strategic bonds were formed via a Nicholas reaction. Name-ly, deformylflustrabromine (100), 200 (-)-allocolchicine (101), 201 velloziolide (102), 202 teurilene (103), 203 (±)-microstegiol (104), 204,205 (-)-isolaure-pinnacin (105) and (+)rogoioloxepane A (106), 206 (+)-cis/(-)-trans-lauthisan (107) and (+)-cis/(-)-trans-obtusan (108), 207 (+)-laurencin (109), 208 as well as formal synthesis and approaches towards the frameworks of icetexane and faveline ring-systems, 209 the framework of solanoeclepin A, 210 and natural product related benzopyran 211 and dibenzocyclooctynes 212 have been described.…”

Section: Scheme 60mentioning

confidence: 99%

Cobalt-Catalysed Bond Formation Reactions; Part 2

Röse

Hilt

2015

Synthesis

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This review summarises the cobalt-catalysed reactions of the years 2008 through 2014. Covered are addition reactions, such as the hydrogenation of double bonds, the addition of C-H bonds to double and triple bonds, C-H activation reactions, cobalt-catalysed cross-coupling reactions and selected additions of H-B and H-Si bonds to unsaturated starting materials. The cobalt-catalysed cycloadditions range from cyclopropanations, [2+2], Pauson-Khand reactions, [2+2+2], [4+2], [6+2] cycloadditions as well as benzannulations. Also covered are Nicholas reactions, cobalt-catalysed Jacobsen's kinetic resolution of epoxides as well as selected miscellaneous cobalt-catalysed processes mainly for carbon-carbon bond formations. 1 Introduction 2 Addition Reactions 3 Homo-and Cross-Coupling Reactions 4 Jacobsen Kinetic Resolution of Epoxides 5 Nicholas Reactions 6 Cycloaddition Reactions 7 Miscellaneous 8 Conclusion

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Epoxide‐Opening Cascades Triggered by a Nicholas Reaction: Total Synthesis of Teurilene

Cited by 42 publications

References 43 publications

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

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

Ring Expansions of Oxiranes and Oxetanes

Cobalt-Catalysed Bond Formation Reactions; Part 2

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