Convergent Synthesis of Pancratistatin from Piperonal and Xylose

Johan Hygum Dam, Robert Madsen

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Abstract

A synthesis of the antitumour agent pancratistatin is described from piperonal and D-xylose. Piperonal is converted into cinnamyl bromide 11 while methyl 5-iodoribofuranoside 12 is derived from xylose. The allylic bromide and the iodocarbohydrate are combined in a zinc-mediated tandem reaction to afford a highly functionalised 1,7-diene, which is then converted into the corresponding cyclohexene by ring-closing olefin metathesis. Subsequent Overman rearrangement, dihydroxylation and deprotection afford the natural product in a total of 25 steps from the two starting materials. The longest linear sequence is from piperonal and gives rise to pancratistatin in 18 steps and 7.0% overall yield. (
Original languageEnglish
JournalEuropean Journal of Organic Chemistry
Issue number27
Pages (from-to)4666-4673
ISSN1434-193X
DOIs
Publication statusPublished - 2009

Keywords

  • Natural products
  • Total synthesis
  • Metathesis
  • Allylation
  • Antitumour agents

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