Catalytic enantioselective synthesis of a novel inhibitor of ceramide trafficking, (1R,3R)-N-(3-hydroxy-1-hydroxymethyl-3-phenylpropyl)dodecanamide (HPA-12)

Keywords

Chemistry, Enantioselective synthesis, Ceramide, Hydroxymethyl, Catalysis

References

• Total synthesis and structural elucidation of khafrefungin.Takeshi Wakabayashi, Kouhei Mori, Shū Kobayashi — 2001
• Asymmetric Synthesis of Antifungal Agents Sphingofungins Using Catalytic Asymmetric Aldol ReactionsSusumu Kobayashi, Takaaki Hayashi, S. IWAMOTO — 1996
• Convergent total synthesis of khafrefungin and its inhibitory activity of fungal sphingolipid syntheses.Shū Kobayashi, Kouhei Mori, Takeshi Wakabayashi — 2001
• Sphingolipids-Their Metabolic Pathways and the Pathobiochemistry of Neurodegenerative Diseases.Thomas Kolter, Konrad Sandhoff — 1999
• Diastereoselective reduction of acyclic N-aryl-β-amino ketonesRonaldo A. Pilli, Dennis Russowsky, Luiz C. Dias — 1990
• CATALYTIC ENANTIOSELECTIVE MANNICH-TYPE REACTIONS USING A NOVEL CHIRAL ZIRCONIUM CATALYSTHaruro Ishitani, Masaharu Ueno, Shū Kobayashi — 1997
• Enantioselective Mannich-Type Reactions Using a Novel Chiral Zirconium Catalyst for the Synthesis of Optically Active β-Amino Acid DerivativesHaruro Ishitani, Masaharu Ueno, Shū Kobayashi — 2000
• Catalytic Asymmetric Syntheses of Antifungal Sphingofungins and Their Biological Activity as Potent Inhibitors of Serine Palmitoyltransferase (SPT)Shū Kobayashi, Takayuki Furuta, Takaomi Hayashi — 1998
• Asymmetric Synthesis of Antifungal Agents Sphingofungins Using Catalytic Asymmetric Aldol ReactionsShū Kobayashi, Takaomi Hayashi, Shunsuke Iwamoto — 1996

Cited by

• Revised stereochemistry of ceramide-trafficking inhibitor HPA-12 by X-ray crystallography analysis.Jeffrey Pfeffer — 2013
• BF3-Mediated cis-Selective Cycloaddition of O-Silyloxime with Alkenes.Nobuyoshi Morita, Rina Kono, Kenji Fukui — 2015
• Synthesis of novel and non-natural ceramide analogues derived from l-glutamic acidKeiji Shikata, Hideki Azuma, Taro Tachibana — 2002
• Identification of Novel CERT Ligands as Potential Ceramide Trafficking InhibitorsCécile Santos, Frédéric Rogriguez, Virginie Garcia — 2014
• The synthesis of Fmoc-O-allyl β-serineYlva E. Bergman, Marisa Ciampini, Sania Jalal — 2008
• Enamides and enecarbamates as nucleophiles in stereoselective C-C and C-N bond-forming reactions.Ryosuke Matsubara, Shū Kobayashi — 2008
• Organocatalytic Asymmetric Mannich Reactions: New Methodology, Catalyst Design, and Synthetic ApplicationsAmal Ting, Scott E. Schaus — 2007
• An air-stable chiral Hf-based catalyst for asymmetric Mannich-type reactionsShū Kobayashi, Ryo Yazaki, Kazutaka Seki — 2007
• Stereoselective synthesis of (−)-allosedamine and (1R,3R)-HPA-12 from β-p-toluenesulfonamido-γ,δ-unsaturated sulfoxide☆Sadagopan Raghavan, A. Rajender — 2004
• The CERT antagonist HPA-12: first practical synthesis and individual binding evaluation of the four stereoisomers.Cécile Santos, Laurence Fleury, Frédéric Rodriguez — 2015
• Catalytic, asymmetric Mannich-type reactions of N-acylimino esters for direct formation of N-acylated amino acid derivatives. Efficient synthesis of a novel inhibitor of ceramide trafficking, HPA-12.Shū Kobayashi, Ryosuke Matsubara, H. Kitagawa — 2002
• Neue Entwicklungen in der asymmetrischen Mehrkomponenten‐ReaktionDiego J. Ramón, Miguel Yus — 2005
• A biologically relevant ceramide fluorescent probe to assess the binding of potential ligands to the CERT transfer proteinStéphanie Combemale, Cécile Santos, Frédéric Rodriguez — 2013
• Asymmetric multicomponent reactions (AMCRs): the new frontier.Diego J. Ramón, Miguel Yus — 2005
• Catalytic enantioselective formation of C-C bonds by addition to imines and hydrazones: a ten-year update.Shū Kobayashi, Yuichiro Mori, John Fossey — 2011
• Asymmetric Synthesis and Binding Study of New Long-Chain HPA-12 Analogues as Potent Ligands of the Ceramide Transfer Protein CERT.Andrej Ďuriš, Adam Daı̈ch, Cécile Santos — 2016
• Organocatalytic route to enantioselective synthesis of ceramide trafficking inhibitor HPA-12Komal G. Lalwani, Arumugam Sudalai — 2016
• Chemistry and Biology of HPAs: A Family of Ceramide Trafficking Inhibitors.Dušan Berkeš, Adam Daı̈ch, Cécile Santos — 2016
• A domino Kornblum-DeLaMare/aza-Michael reaction of 3,6-dihydro-1,2-dioxines and application to the synthesis of the ceramide transport inhibitor (±)-HPA-12Sarah V. A.-M. Legendre, Martyn Jevric, Julian Klepp — 2017
• A chemoenzymatic synthesis of ceramide trafficking inhibitor HPA-12Seema V. Kanojia, Sucheta Chatterjee, Subrata Chattopadhyay — 2019

Related papers

• Recent developments in enantioselective iron-catalyzed transformationsHélène Pellissier — 2019
• Methods of Asymmetric Synthesis—Enantioselective Catalytic HydrogenationYoshiharu Izumi — 1971
• Alternative Synthetic Strategiesfor Enantioselective Construction of Halogenated ChiralCarbon CentersKazutaka Shibatomi — 2010
• Titanocene-Catalysed Enantioselective Opening ofmeso-EpoxidesAndreas Gansäuer, Harald Bluhm, Thorsten Lauterbach — 2001
• Enantioselective preparation of C2-symmetrical 1,4-diolsStephan Vettel, Paul Knochel — 1994
• The First Catalytic Enantioselective Synthesis of (R)-(+) LasiodiplodinGraham B. Jones, Robert S. Huber — 1993
• Enantioselective biomimetic polyene cyclization of polyprenoids : Long-sought enantioselective reaction induced by a chiral halonium ionAkira Sakakura, Kazuaki Ishihara — 2007
• Enantioselective Cobalt-Catalyzed C-H FunctionalizationMengchun Ye, Weiwei Xu — 2022