Literature DB >> 15162217

A practical synthesis of D-erythro-sphingosine using a cross-metathesis approach.

Staffan Torssell1, Peter Somfai.   

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 5 in steps and 51% overall yield.

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Year:  2004        PMID： 15162217     DOI： 10.1039/b403568b

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  7 in total

1.  Diastereoselective Nickel-Catalyzed Reductive Couplings of Aminoaldehydes and Alkynylsilanes: Application to the Synthesis of D-erythro-Sphingosine.

Authors:  Kanicha Sa-Ei; John Montgomery
Journal:  Tetrahedron       Date:  2009-09-15       Impact factor: 2.457

2.  Synthesis and properties of a photoactivatable analogue of psychosine (beta-Galactosylsphingosine).

Authors:  Ravi S Lankalapalli; Attila Baksa; Károly Liliom; Robert Bittman
Journal:  ChemMedChem       Date:  2010-05-03       Impact factor: 3.466

3.  Stereoselective Synthesis of trans-Olefins by the Copper-Mediated S(N)2' Reaction of Vinyl Oxazines with Grignard Reagents. Asymmetric Synthesis of D-threo-Sphingosines.

Authors:  Om V Singh; Hyunsoo Han
Journal:  Tetrahedron Lett       Date:  2007       Impact factor: 2.415

4.  D-Glucosamine-derived synthons for assembly of L-threo-sphingoid bases. Total synthesis of rhizochalinin C.

Authors:  Jaeyoung Ko; Tadeusz F Molinski
Journal:  J Org Chem       Date:  2012-12-27       Impact factor: 4.354

5.  Caged ceramide 1-phosphate analogues: synthesis and properties.

Authors:  Ravi S Lankalapalli; Alberto Ouro; Lide Arana; Antonio Gómez-Muñoz; Robert Bittman
Journal:  J Org Chem       Date:  2009-11-20       Impact factor: 4.354

6.  A concise and scalable synthesis of high enantiopurity (-)-D-erythro-sphingosine using peptidyl thiol ester-boronic acid cross-coupling.

Authors:  Hao Yang; Lanny S Liebeskind
Journal:  Org Lett       Date:  2007-07-04       Impact factor: 6.005

7.  Synthesis of truncated analogues of the iNKT cell agonist, α-galactosyl ceramide (KRN7000), and their biological evaluation.

Authors:  Natacha Veerapen; Faye Reddington; Mariolina Salio; Vincenzo Cerundolo; Gurdyal S Besra
Journal:  Bioorg Med Chem       Date:  2010-11-19       Impact factor: 3.641
  7 in total

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