Synthesis of new ceramide analogues with allene in the sphingoid backbone

References

• Brodesser, S.; Sawatzki, P.; Kolter, T. Bioorganic Chemistry of Ceramide. Eur. J. Org. Chem. 2003, 2003, 2021–2034. DOI: 10.1002/ejoc.200200518.
   Web of Science ®Google Scholar
• Ďuriš, A.; Daïch, A.; Santos, C.; Fleury, L.; Ausseil, F.; Rodriguez, F.; Ballereau, S.; Génisson, Y.; Berkeš, D. Asymmetric Synthesis and Binding Study of New Long-Chain HPA-12 Analogues as Potent Ligands of the Ceramide Transfer Protein CERT. Chemistry 2016, 22, 6676–6686. DOI: 10.1002/chem.201505121.
   PubMed Web of Science ®Google Scholar
• Morad, S. A. F.; Cabot, M. C. Ceramide-Orchestrated Signalling in Cancer Cells. Nat. Rev. Cancer 2013, 13, 51–65. DOI: 10.1038/nrc3398.
   PubMed Web of Science ®Google Scholar
• Ogretmen, B.; Hannun, Y. A. Biologically Active Sphingolipids in Cancer Pathogenesis and Treatment. Nat. Rev. Cancer 2004, 4, 604–616. DOI: 10.1038/nrc1411.
   PubMed Web of Science ®Google Scholar
• Gourier, C.; Pincet, F.; Perez, E.; Zhang, Y.; Zhu, Z.; Mallet, J. M.; Sinaÿ, P. The Natural LewisX-Bearing Lipids Promote Membrane Adhesion: influence of Ceramide on Carbohydrate-Carbohydrate Recognition. Angew. Chem. Int. Ed. Engl. 2005, 44, 1683–1687. DOI: 10.1002/anie.200461224.
   PubMed Web of Science ®Google Scholar
• Czubowicz, K.; Jęśko, H.; Wencel, P.; Lukiw, W. J.; Strosznajder, R. P. The Role of Ceramide and Sphingosine-1-Phosphate in Alzheimer's Disease and Other Neurodegenerative Disorders. Mol. Neurobiol. 2019, 56, 5436–5455. DOI: 10.1007/s12035-018-1448-3.
   PubMed Web of Science ®Google Scholar
• Liu, J.; Beckman, B. S.; Foroozesh, M. A Review of Ceramide Analogs as Potential Anticancer Agents. Future Med Chem. 2013, 5, 1405–1421. DOI: 10.4155/fmc.13.107.
   PubMed Web of Science ®Google Scholar
• Takasugi, N.; Sasaki, T.; Shinohara, M.; Iwatsubo, T.; Tomita, T. Synthetic Ceramide Analogues Increase Amyloid-β 42 Production by Modulating γ-Secretase Activity. Biochem. Biophys. Res. Commun. 2015, 457, 194–199. DOI: 10.1016/j.bbrc.2014.12.087.
   PubMed Web of Science ®Google Scholar
• Antoon, J. W.; Liu, J.; Gestaut, M. M.; Burow, M. E.; Beckman, B. S.; Foroozesh, M. Design, Synthesis, and Biological Activity of a Family of Novel Ceramide Analogues in Chemoresistant Breast Cancer Cells. J. Med. Chem. 2009, 52, 5748–5752. DOI: 10.1021/jm9009668.
   PubMedGoogle Scholar
• Chang, Y. T.; Choi, J.; Ding, S.; Prieschl, E. E.; Baumruker, T.; Lee, J. M.; Chung, S. K.; Schultz, P. G. The Synthesis and Biological Characterization of a Ceramide Library. J. Am. Chem. Soc. 2002, 124, 1856–1857. DOI: 10.1021/ja017576o.
   PubMed Web of Science ®Google Scholar
• He, L.; Byun, H. S.; Smit, J.; Wilschut, J.; Bittman, R. Enantioselective Synthesis of a Novel Trans Double Bond Ceramide Analogue via Catalytic Asymmetric Dihydroxylation of an Enyne. The Role of the Trans Double Bond of Ceramide in the Fusion of Semliki Forest Virus with Target Membranes. J. Am. Chem. Soc. 1999, 121, 3897–3903. DOI: 10.1021/ja981493z.
   Web of Science ®Google Scholar
• Struckhoff, A. P.; Bittman, R.; Burow, M. E.; Clejan, S.; Elliott, S.; Hammond, T.; Tang, Y.; Beckman, B. S. Novel Ceramide Analogs as Potential Chemotherapeutic Agents in Breast Cancer. J. Pharmacol. Exp. Ther. 2004, 309, 523–532. DOI: 10.1124/jpet.103.062760.
   PubMed Web of Science ®Google Scholar
• Chun, J.; He, L.; Byun, H. S.; Bittman, R. Synthesis of Ceramide Analogues Having the C(4)-C(5) Bond of the Long-Chain Base as Part of an Aromatic or Heteroaromatic System. J. Org. Chem. 2000, 65, 7634–7640. DOI: 10.1021/jo001227f.
   PubMed Web of Science ®Google Scholar
• Chun, J.; Li, G.; Byun, H. S.; Bittman, R. S. Synthesis of New Trans Double-Bond Sphingolipid Analogues: Delta(4,6) and Delta(6) Ceramides. J. Org. Chem. 2002, 67, 2600–2605. DOI: 10.1021/jo0162639.
   PubMed Web of Science ®Google Scholar
• Chun, J.; Byun, H. S.; Bittman, R. First Asymmetric Synthesis of 6-Hydroxy-4-Sphingenine-Containing Ceramides. Use of Chiral Propargylic Alcohols to Prepare a Lipid Found in Human Skin. J. Org. Chem. 2003, 68, 348–354. DOI: 10.1021/jo026240+.
   PubMed Web of Science ®Google Scholar
• Chun, J.; Byun, H. S.; Arthur, G.; Bittman, R. Synthesis and Growth Inhibitory Activity of Chiral 5-Hydroxy-2-N-Acyl-(3E)-Sphingenines: ceramides with an Unusual Sphingoid Backbone. J. Org. Chem. 2003, 68, 355–359. DOI: 10.1021/jo026242u.
   PubMed Web of Science ®Google Scholar
• Krause, N.; Hashmi, A. S. K. Modern Allene Chemistry. Wiley-VCH: Weinheim, 2004.
   Google Scholar
• Brusoe, A. T.; Alexanian, E. J. Rhodium(I)-Catalyzed Ene-Allene-Allene [2 + 2+2] Cycloadditions: stereoselective Synthesis of Complex Trans-Fused Carbocycles. Angew. Chem. Int. Ed. Engl. 2011, 50, 6596–6600. DOI: 10.1002/anie.201100272.
   PubMed Web of Science ®Google Scholar
• Hoffmann-Röder, A.; Krause, N. Synthesis and Properties of Allenic Natural Products and Pharmaceuticals. Angew. Chem. Int. Ed. Engl. 2004, 43, 1196–1216. DOI: 10.1002/anie.200300628.
   PubMed Web of Science ®Google Scholar
• Kang, S. K.; Kim, S. G.; Cho, D.-G. Synthesis of α-Allenic Alcohols from Propargylic Cyclic Carbonates and Sulfites. Tetrahedron: Asymmetry 1992, 3, 1509–1510. DOI: 10.1016/S0957-4166(00)86046-2.
   Google Scholar
• Marshall, J. A.; Adams, N. D. Diastereoselective and Enantioselective Synthesis of Homopropargyl and Allenylcarbinols from Nonracemic Propargyl Mesylates via the Derived Allenyl and Propargyl Trichlorosilanes. J. Org. Chem. 1997, 62, 8976–8977. DOI: 10.1021/jo971853l.
   Web of Science ®Google Scholar
• Ito, H.; Nakamura, T.; Taguchi, T.; Hanzawa, Y. Preparation and Reactions of Allenic Zirconium Species from Propargylic Ether Derivatives. Tetrahedron Lett. 1992, 33, 3769–3772. DOI: 10.1016/0040-4039(92)80020-K.
   Web of Science ®Google Scholar
• Kobayashi, K.; Naka, H.; Wheatley, A. E. H.; Kondo, Y. Organozinc Reagents in DMSO Solvent: remarkable Promotion of SN2' Reaction for Allene Synthesis. Org. Lett. 2008, 10, 3375–3377. DOI: 10.1021/ol801249w.
   PubMed Web of Science ®Google Scholar
• Zweifel, G.; Hahn, G. Allenic Zinc Reagents. A Remarkably Regio- and Diastereoselective Synthesis of 2-Substituted Homopropargylic Alcohols. J. Org. Chem. 1984, 49, 4565–4567. DOI: 10.1021/jo00197a059.
   Web of Science ®Google Scholar
• (a) Cowie, J. S.; Landor, P. D.; Landor, S. R. Allenes. Part XXIV. Preparation of α-Allenic Alcohols from the Mono-O-tetrahydropyran-2-yl Derivatives of Butyne-1,4-diols. J. Chem. Soc. Perkin. 1973, 1, 720–724. (b)
   Google Scholar
  Olsson, L.-I.; Claesson, A.; Boll, P. M.; Hope, H.; Christensen, A.; Schroll, G. Chiral Allenic Alcohols from Addition-Elimination  Reactions of Acetylenes with Lithium Aluminium Hydride. Acta Chem. Scand. 1977, 31b, 614–618. DOI: 10.3891/acta.chem.scand.31b-0614.
   Google Scholar
• VanBrunt, M. P.; Standaert, R. F. A Short Total Synthesis of (+)-Furanomycin. Org. Lett. 2000, 2, 705–708. DOI: 10.1021/ol005569j.
   PubMed Web of Science ®Google Scholar
• Bertozzi, F.; Crotti, P.; Macchia, F.; Pineschi, M.; Arnold, A.; Feringa, B. L. A New Diastereo- and Enantioselective Copper-Catalyzed Conversion of Alkynyl Epoxides into α-Allenic Alcohols. Tetrahedron Lett 1999, 40, 4893–4896. DOI: 10.1016/S0040-4039(99)00905-3.
   Web of Science ®Google Scholar
• Konoike, T.; Araki, Y. Concise Allene Synthesis from Propargylic Alcohols by Hydrostannation and Deoxystannylation: A New Route to Chiral Allenes. Tetrahedron Lett. 1992, 33, 5093–5096. DOI: 10.1016/S0040-4039(00)61198-X.
   Web of Science ®Google Scholar
• Linstrumelle, G.; Michelot, D. J. Simple Route to Mono-, di-, and Tri-Substituted Allenic Compounds. J. Chem. Soc, Chem. Commun. 1975, 14, 561–562. DOI: 10.1039/c39750000561.
   Google Scholar
• Montury, M.; Gore, J. New Preparation of Bromoallenes. Synth. Commun. 1980, 10, 873–879. DOI: 10.1080/00397918008062772.
   Web of Science ®Google Scholar
• Greaves, P. M.; Landor, S. R.; Lwanga, M. M. Reactions of Grignard Reagents from 1-Halogenoallenes. Allenes—XXXIII. Tetrahedron 1975, 31, 3073–3075. DOI: 10.1016/0040-4020(75)80150-5.
   Web of Science ®Google Scholar
• Claesson, A.; Olsson, L. I. Allenes and Acetylenes. 22. Mechanistic Aspects of the Allene-Forming Reductions (SN2' Reaction) of Chiral Propargylic Derivatives with Hydride Reagents. J. Am. Chem. Soc. 1979, 101, 7302–7311. DOI: 10.1021/ja00518a028.
   Web of Science ®Google Scholar
• Keck, G. E.; Webb, R. R. A Versatile Method for the Preparation of Allenic Alcohols. Tetrahedron Lett. 1982, 23, 3051–3054. DOI: 10.1016/S0040-4039(00)87530-9.
   Web of Science ®Google Scholar
• Biollaz, M.; Landeros, R. M.; Cuellar, L.; Crabbe, P.; Rooks, W.; Edwards, J. A.; Fried, J. H. 17-Alpha-Propadienyl-19-Nortestosterone and Related Compounds. A New Series of Potent Orally Active Progestogens. J. Med. Chem. 1971, 14, 1190–1192. DOI: 10.1021/jm00294a012.
   PubMed Web of Science ®Google Scholar
• Claesson, A.; Olsson, L. I.; Sullivan, G. R.; Mosher, H. S. Allenes and Acetylenes. IX. Synthesis of Chiral Allenic Alcohols and Nuclear Magnetic Resonance Determination of Their Enantiomeric Purities Using a Chiral Lanthanide Shift Reagent. J. Am. Chem. Soc. 1975, 97, 2919–2921. DOI: 10.1021/ja00843a061.
   Web of Science ®Google Scholar
• Doutheau, A.; Saba, A.; Gore, J. Synthesis of α-Functionalized Allenes. Synth. Commun. 1982, 12, 557–563. DOI: 10.1080/00397918208063695.
   Web of Science ®Google Scholar