Synthesis of lupinacidins A and B via sequential cycloaddition-double elimination

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2 Citations (Scopus)

Abstract

The first synthesis of lupinacidins A and B, tumor cell invasion inhibitors of microbial origin, has been achieved in four operational steps from 3-methoxy-2-methyl-2-cyclohexenone via the Diels-Alder cycloaddition of a conjugated cyclohexadiene derivative with a juglone-derived sulfinyl quinone followed by sequential elimination of a sulfenic acid and ethylene to afford protected forms of the target molecules.

Original languageEnglish
Pages (from-to)4570-4572
Number of pages3
JournalTetrahedron Letters
Volume51
Issue number34
DOIs
Publication statusPublished - 2010 Aug 25

Keywords

  • Anthraquinone
  • Antitumor
  • Diels-Alder reaction
  • Lupinacidin

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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