Synthesis of spirastrellolide A fragments for structure elucidation

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Abstract

A stereocontrolled synthesis of two diastereomeric C1-C 22 fragments of spirastrellolide A consistent with reported spectroscopic data has been achieved to aid in a complete configurational assignment of this structurally novel and potent antimitotic natural product. A highly convergent coupling of two enantiomeric C1-C10 methyl ketone fragments with an enantiopure C11-C22 spiroketal aldehyde produced the C1-C22 fragments with a longest linear sequence of 13 steps from commercially available starting materials.

Original languageEnglish (US)
Pages (from-to)853-856
Number of pages4
JournalSynlett
Issue number6
DOIs
Publication statusPublished - Apr 4 2006

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Keywords

  • Asymmetric synthesis
  • Natural products
  • Spiro compounds
  • Structure elucidation
  • Total synthesis

ASJC Scopus subject areas

  • Organic Chemistry

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