Journal Article10.1039/B403568B
A practical synthesis of D-erythro-sphingosine using a cross-metathesis approach
Staffan Torssell,Peter Somfai +1 more
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TL;DR: In this paper, a short and practical synthesis of D-erythro-sphingosine was described, starting from a vinylepoxide and an E-selective cross-metathesis, affording the target molecule in 5 steps and 51% overall yield.
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Abstract: Starting from a vinylepoxide, a short and practical synthesis of D-erythro-sphingosine is described. The key transformations are a regioselective opening of the vinylepoxide and an E-selective cross-metathesis, affording the target molecule in 5 steps and 51% overall yield.
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Citations
Synthesis of borondipyrromethene (BODIPY)-labeled sphingosine derivatives by cross-metathesis reaction
Carsten Peters,Andreas Billich,Michael Ghobrial,Klemens Högenauer,Thomas Ullrich,Peter Nussbaumer +5 more
TL;DR: A new efficient and flexible synthesis of fluorescently labeled sphingosine derivatives from commercially available Garner aldehyde is described, and one of these derivatives was identified as the first reported selective substrate for SPHK-1.
95
Versatile synthetic method for sphingolipids and functionalized sphingosine derivatives via olefin cross metathesis.
TL;DR: A highly efficient and versatile method for the synthesis of various sphingolipids, such as sphingomyelin, ceramide, sphingosine, sphedosine 1-phosphate, and functionalized sphingoine derivatives, was established by two types of combinations of the olefin cross metathesis reaction.
90
Chemical and chemoenzymatic synthesis of S-linked ganglioside analogues and their protein conjugates for use as immunogens.
TL;DR: The initial results suggest that in fact these antigens are viable immunogens and furthermore, that immune sera cross reacts with O-gangliosides in the context of a heterologous glycoprotein conjugate.
74
A Concise and Scalable Synthesis of High Enantiopurity (−)-d-erythro-Sphingosine Using Peptidyl Thiol Ester−Boronic Acid Cross-Coupling
Hao Yang,Lanny S. Liebeskind +1 more
TL;DR: A short and efficient synthesis of high enantiopurity (-)-D-erythro-sphingosine has been achieved in 71% yield over 6 steps from N-Boc-L-serine.
61
High-yielding synthesis of sphingoid-type bases.
TL;DR: An efficient methodology for the synthesis of sphingoid-type bases involves the stereoselective addition of a racemic 3-alkoxy allenylzinc to enantiopure N-tert-butylsulfinyl imines and a cross-metathesis reaction as the key steps.
58
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Ruthenium Carbene Complexes with N,N‘-Bis(mesityl)imidazol-2-ylidene Ligands: RCM Catalysts of Extended Scope
TL;DR: The ruthenium carbene complexes 3a,b bearing imidazol-2-ylidene ligands constitute excellent precatalysts for ring-closing metathesis (RCM) reactions allowing the formation of tri- and tetrasubstituted cycloalkenes and their reactivity was found to be highly dependent on the reaction medium.
Reactions that proceed with a combination of enantiotopic group and diastereotopic face selectivity can deliver products with very high enantiomeric excess: experimental support of a mathematical model
TL;DR: In this article, the epoxyalcools of Sharpless et al. were augmented with le degre d'achevement de the reaction of the reaction in order to improve the performance.
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Glycobiology: a growing field for drug design
TL;DR: Substantial information on protein-carbohydrate interactions in physiological and pathological situations substantiates the intuitive belief in carbohydrates as candidates for drug design and will inspire new approaches to the treatment of several important medical conditions where existing methods are insufficient.
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Sphingosine, an Enigmatic Lipid: A Review of Recent Literature Syntheses
Abstract: Sphingolipids are ubiquitous membrane components of essentially all eukaryotic cells. There are currently over 300 known sphingolipids with distinct head groups all containing the sphingoid base backbone. In addition to D erythro -sphingosine there are over 60 other sphingoid base structures found elsewhere in nature. Sphingosine has been a target of synthetic interest since mid-1950 ́s and well over 50 syntheses have since been published. In this review we describe the sphingosine syntheses until the end of 1997.
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