Synthesis of d-erythro-Dihydrosphingosine and d-xylo-Phytosphingosine from a Serine-Derived 1,5-Dioxaspiro[3.2]hexane Template
- 18 April 2002
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 4 (10) , 1719-1722
- https://doi.org/10.1021/ol0200448
Abstract
A serine-derived 1,5-dioxaspiro[3.2]hexane template is shown to be a useful precursor for both aminodiol and aminotriol sphingoid bases by its conversion to d-erythro-dihydrosphingosine and d-xylo-phytoshingosine.Keywords
This publication has 13 references indexed in Scilit:
- Phytosphingosines — a facile synthesis and spectroscopic protocol for configurational assignmentTetrahedron, 1999
- Ring Opening of 1,5-Dioxaspiro[3.2]hexanes: Selective Preparation of α-Heterofunctionalized-β‘-hydroxy Ketones or 2,2-Disubstituted OxetanesOrganic Letters, 1999
- THE CD1 SYSTEM: Antigen-Presenting Molecules for T Cell Recognition of Lipids and GlycolipidsAnnual Review of Immunology, 1999
- Glycolipids from Sponges. 6.1 Plakoside A and B, Two Unique Prenylated Glycosphingolipids with Immunosuppressive Activity from the Marine Sponge Plakortis simplexJournal of the American Chemical Society, 1997
- CD1d-Restricted and TCR-Mediated Activation of V α 14 NKT Cells by GlycosylceramidesScience, 1997
- Sphingolipids: metabolism and cell signallingPublished by Elsevier ,1996
- Structure-Activity Relationship of .alpha.-Galactosylceramides against B16-Bearing MiceJournal of Medicinal Chemistry, 1995
- Stereochemistry associated with the addition of 2-(trimethylsilyl)thiazole to differentially protected .alpha.-amino aldehydes. Applications toward the synthesis of amino sugars and sphingosinesThe Journal of Organic Chemistry, 1990
- 2-thienyl(cyano)copper lithium. A lower order, “cuprate in a bottle” precursor to higher order reagentsTetrahedron Letters, 1987
- New nitrogenous sesquiterpenes from the marine sponge Axinella cannabinaThe Journal of Organic Chemistry, 1984