[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.
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Synthesis of epi-oxetin via a serine-derived 2-methyleneoxetane.
J Org Chem
January 2008
Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, USA.
The unique reactivity of 2-methyleneoxetanes and 1,5-dioxaspiro[3.2]hexanes has been exploited for the synthesis of epi-oxetin (26), an oxetane-containing beta-amino acid. While the preparation of the natural product oxetin (1) was the original goal, the unexpected diastereoselectivity of an precedented reduction provided the epi-oxetin framework.
View Article and Find Full Text PDFSynthesis of D-erythro-dihydrosphingosine and D-xylo-phytosphingosine from a serine-derived 1,5-dioxaspiro[3.2]hexane template.
Org Lett
May 2002
Department of Chemistry, University of Connecticut, Storrs 06269-3060, USA.
[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.
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