Synthesis of D-erythro-dihydrosphingosine and D-xylo-phytosphingosine from a serine-derived 1,5-dioxaspiro[3.2]hexane template.
[reaction: see text] 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.
Ndakala
Albert J
AJ
Department of Chemistry, University of Connecticut, Storrs 06269-3060, USA.
Hashemzadeh
Mehrnoosh
M
So
Regina C
RC
Howell
Amy R
AR
D000818:Animals; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D007166:Immunosuppressive Agents / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D011161:Porifera / Q000737:chemistry*; D012694:Serine / Q000737:chemistry*; D013110:Sphingosine / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013698:Templates, Genetic
C458142:1,5-dioxaspiro(3.2)hexane; D006571:Heterocyclic Compounds; D007166:Immunosuppressive Agents; D007202:Indicators and Reagents; D013141:Spiro Compounds; C458141:erythro-dihydrosphingosine; C458140:xylo-phytosphingosine; D012694:Serine; D013110:Sphingosine