Enantioselective syntheses of pachastrissamine and jaspine A via hydroxylactonization of a chiral epoxy ester

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Abstract

A new enantioselective total synthesis of pachastrissamine (jaspine B) was achieved from a known α,β-unsaturated aldehyde by utilizing Córdova's asymmetric epoxidation as the chirality-inducing step. The 2,3-cis stereochemistry of pachastrissamine was established via intramolecular epoxide ring opening of a γ,δ-epoxy-α,β-unsaturated ester intermediate coupled with oxy-Michael cyclization. Treatment of pachastrissamine with tetrahydro-2-furanol under acidic conditions led to smooth oxazolidine ring formation, furnishing jaspine A in a high yield.

Original languageEnglish
Pages (from-to)152-157
Number of pages6
JournalBioscience, Biotechnology and Biochemistry
Volume74
Issue number1
DOIs
Publication statusPublished - 2010

Keywords

  • Cytotoxic
  • Hetrocycle
  • Jaspine
  • Pachastrissamine
  • Phytosphingosine

ASJC Scopus subject areas

  • Biotechnology
  • Analytical Chemistry
  • Biochemistry
  • Applied Microbiology and Biotechnology
  • Molecular Biology
  • Organic Chemistry

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