An efficient high-yield synthesis of D-ribo-phytosphingosine

Org Lett. 2006 Jul 20;8(15):3303-5. doi: 10.1021/ol0612096.

Abstract

[Structure: see text] [4R-[4alpha(S),5alpha]]-2,2-Dimethyl-4-(2-oxo-5-vinyl[1,3]dioxolan-4-yl)oxazolidine-3-carboxylic acid tert-butyl ester 5a, obtained in excellent yield and diastereoselectivity by the alpha-hydroxyallylation of the Garner aldehyde (4), is exploited in a novel high-yield synthesis of D-ribo-phytosphingosine (8), using microwave-enhanced cross metathesis as the key step in the chain elongation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Catalysis
  • Molecular Structure
  • Sphingosine / analogs & derivatives*
  • Sphingosine / chemical synthesis
  • Sphingosine / chemistry
  • Stereoisomerism

Substances

  • Aldehydes
  • phytosphingosine
  • Sphingosine