Total synthesis of pachastrissamine together with its 4-epi-congener via [3,3]-sigmatropic rearrangements and antiproliferative/cytotoxic evaluation

Martinková, Miroslava; Mezeiová, Eva; Fabišíková, Milica; Gonda, Jozef; Pilátová, Martina; Mojžiš, Ján

doi:10.1016/j.carres.2014.11.004

Cited by 19 publications

(10 citation statements)

References 63 publications

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“…Without further purification, the sulfonate ester moiety was introduced via a Horner–Wadsworth–Emmons reaction with phosphonate 13 to give vinyl sulfonate 14 as a mixture of E / Z alkenes which was used without purification . Sodium borohydride reduction of the crude 14 in a Michael reaction was stereoselective because of the steric effect of the acetal moiety and yielded a single isomer of compound 15 in 48% overall yield over three steps . The crucial di-acetate synthon 16 to be used for the incorporation of each of the nucleobases was obtained in a acetal deprotection/acetylation step in 66% yield …”

Section: Resultsmentioning

confidence: 99%

“…23 Sodium borohydride reduction of the crude 14 in a Michael reaction was stereoselective because of the steric effect of the acetal moiety and yielded a single isomer of compound 15 in 48% overall yield over 3 steps. 24 The crucial di-acetate synthon 16 to be used for incorporation each of the nucleobases, was obtained in a acetal deprotection/ acetylation step in 66% yield. 25 Scheme 3.…”

Section: Scheme 2 Side Reaction Of Azide With the Sulfonate Estermentioning

confidence: 99%

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Molecular Construction of Sulfonamide Antisense Oligonucleotides

et al. 2019

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Section: Resultsmentioning

confidence: 99%

Section: Scheme 2 Side Reaction Of Azide With the Sulfonate Estermentioning

confidence: 99%

Molecular Construction of Sulfonamide Antisense Oligonucleotides

et al. 2019

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“…The team of Martinková used a carbamate during the synthesis of the chloride salt of pachastrissamine. 90 Less common, the PMB ether was a good protecting and leaving group during the acidpromoted synthesis of spiroketal units of pectenotoxin proposed by Pihko et al. 89 Unfortunately, no matter which the acid tested a mixture of kinetic and thermodynamic spiroketals is observed, with as a best result chloroacetic acid (49% yield with 5% of the epimer).…”

Section: Scheme 25: Thf Formation By Reductive Cyclizationmentioning

confidence: 97%

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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“…9,10) Because of its novel structural features and impressive biological activity, many total syntheses of 1 have been accomplished. [3][4][5][6][7][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30] The stereoisomers of 1 have also been synthesized, 5,6,[20][21][22][23][24][25][26][27][28][29][31][32][33][34][35][36][37][38][39][40] and their biological activity investigated. Interestingly, the 2-epimer 2 6,…”

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confidence: 99%