Syntheses of the C1–C14 and C15–C25 Fragments of Amphidinolide C

Wu, D.

doi:10.1021/ol303515h

Cited by 22 publications

(16 citation statements)

References 43 publications

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“…To date, Hartung , partially explored in terms of scope only a single α,β-unsaturated ester, which provides excellent 2,5- trans diastereoselectivities under reductive termination (Scheme b). Subsequent application of this methodology by Wu and Forsyth in the synthesis of C15–C25 fragments of amphidinolide C3 showed this to be superior to the oxa-Michael strategy . On the basis of these backgrounds, herein, we report a protocol to integrate a sustainable approach for the synthesis of new 2,5- trans -THF nitrile derivatives enabling an easy diversification of 2,5-THF side chain scaffold (Scheme c).…”

Section: Introductionmentioning

confidence: 97%

Cobalt-Catalyzed Stereoselective Synthesis of 2,5-trans-THF Nitrile Derivatives as a Platform for Diversification: Development and Mechanistic Studies

et al. 2018

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A straightforward protocol integrating a sustainable approach for the synthesis of new 2,5- trans-THF nitrile derivatives enabling an easy diversification of its side chain scaffolds is described. The reaction tolerated different aromatic and alkyl substituents, affording the corresponding 2,5- trans-THFs in high diastereoselectivity. A detailed mechanistic study using DFT calculation reveals details of the ligand-exchange step, suggesting an inner-sphere syn attack to form the 2,5- trans stereochemistry as the most likely pathway, excluding the previous cation radical intermediate. The formation of a Co-C intermediate is suggested on the basis of the homolytic cleavage to give the previously proposed free carbon radical intermediate.

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Section: Introductionmentioning

confidence: 97%

Cobalt-Catalyzed Stereoselective Synthesis of 2,5-trans-THF Nitrile Derivatives as a Platform for Diversification: Development and Mechanistic Studies

et al. 2018

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“…A number of laboratories have communicated advances of methodology directed toward the syntheses of fragments of amphidinolide C and its related macrolides . In 2012, Mahapatra and Carter completed the first total syntheses of amphidinolide F and, shortly thereafter, amphidinolide C .…”

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confidence: 99%

Studies of the Enantiocontrolled Synthesis of the C(10)–C(25) Subunit of Amphidinolide C

Williams

Fultz

et al. 2020

Org. Lett.

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A stereocontrolled synthesis of 28, the C(10)–C(25) component of amphidinolide C (1), has been efficiently achieved. Reaction of the dithiane component 21 with nonracemic bis(epoxide) 19 directly affords functionalized 2,5-trans-disubstituted tetrahydrofuran 22. Propargylation is highly diastereoselective for the formation of the desired C(12)–C(13) anti stereochemistry, and the resulting terminal alkyne 25 is utilized for a regioselective syn-silylstannylation. A general strategy is illustrated for sequential replacement of stannyl and silyl substituents of the trisubstituted alkene to yield (E)-alkenyl iodide 28.

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“…In addition, a cobalt catalyzed cyclization process was studied by the team of Forsyth in 2013. 101 They realized the synthesis of the C15-C25 fragment of Amphidinolide C using Hartung's cobalt catalyst (Scheme 31).…”

Section: Scheme 30 : Isomerization -Conjugate Addition For the Formatmentioning

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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Syntheses of the C1–C14 and C15–C25 Fragments of Amphidinolide C

Cited by 22 publications

References 43 publications

Cobalt-Catalyzed Stereoselective Synthesis of 2,5-trans-THF Nitrile Derivatives as a Platform for Diversification: Development and Mechanistic Studies

Cobalt-Catalyzed Stereoselective Synthesis of 2,5-trans-THF Nitrile Derivatives as a Platform for Diversification: Development and Mechanistic Studies

Studies of the Enantiocontrolled Synthesis of the C(10)–C(25) Subunit of Amphidinolide C

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

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