@article { ISI:000249453100008, title = {4-Formylazetidin-2-one as a useful building block for the formal synthesis of xylo-(2S,3R,4R)-phytosphingosine and threo-(2S,3S)-sphingosine}, journal = {Synthesis-Stuttgart }, volume = {17}, number = {17}, year = {2007}, month = {SEP}, pages = {2631-2636}, publisher = {GEORG THIEME VERLAG KG}, type = {Article}, address = {RUDIGERSTR 14, D-70469 STUTTGART, GERMANY}, abstract = {

Stereoselective formal synthesis of xylo-(2S,3R,4R)-phytosphingosine and threo-(2S,3S)-sphingosine is described starting from an enantiopure formyl-substituted P-lactam. Grignard reaction of the N-Boc-protected-beta-lactam carbonyl group, followed by further transformations, provides a common intermediate for xylo-(2S,3R,4R)-phytosphingosine and threo-(2S,3S)-sphingosine.

}, keywords = {azetidin-2-one, beta-lactam, Grignard reaction, Phytosphingosine, Sphingosine}, issn = {0039-7881}, doi = {10.1055/s-2007-983815}, author = {Kale, Ajaykumar S. and Sakle, Prathmesh S. and Gumaste, Vikas K. and Deshmukh, Abdul Rakeeb A. S.} } @article { ISI:000267070700046, title = {Enantioselective total synthesis of (2S,3R,4R)-D-xylo-phytosphingosine from substituted azetidin-2-one}, journal = {Tetrahedron Letters}, volume = {50}, number = {26}, year = {2009}, month = {JUL}, pages = {3296-3298}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

Enantiomerically pure (2S,3R,4R)-D-xylo phytosphingosine is synthesized in 36\% overall yield in seven steps from known beta-lactam (8) derived from D-mannitol triacetonide. (C) 2009 Elsevier Ltd. All rights reserved.

}, keywords = {beta-lactam, Enantioselective synthesis, Sphingosine, Wittig reaction}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2009.02.050}, author = {Pandey, Ganesh and Tiwari, Dharmendra Kumar} } @article { ISI:000341883700033, title = {Flexible, polymer-supported synthesis of sphingosine derivatives provides ceramides with enhanced biological activity}, journal = {Bioorganic \& Medicinal Chemistry}, volume = {22}, number = {19}, year = {2014}, month = {OCT}, pages = {5506-5512}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

A polymer-supported route for the synthesis of sphingosine derivatives is presented based on the C-acylation of polymeric phosphoranylidene acetates with an Fmoc-protected amino acid. The approach enables the flexible variation of the sphingosine tail through a deprotection-decarboxylation sequence followed by E-selective Wittig olefination cleavage. D-Erythro-sphingosine analogs have been synthesized by diastereoselective reduction of the keto group employing LiAlH(O-tBu)(3) as reducing agent. The effect of ceramides and keto-ceramides on the proliferation of three cancer cell lines HEP G-2, PC-12 and HL-60 was investigated and a ceramide containing an aromatic sphingosine tail was identified as being most active. (C) 2014 Elsevier Ltd. All rights reserved.

}, keywords = {Apoptosis, Ceramide, Lipid rafts, Lipids, Sphingosine}, issn = {0968-0896}, doi = {10.1016/j.bmc.2014.07.024}, author = {El-Dahshan, Adeeb and Al-Gharabli, Samer I. and Radetzki, Silke and Al-Tel, Taleb H. and Kumar, Pradeep and Rademann, Joerg} }