Convergent Synthesis of Pancratistatin from Piperonal and Xylose

Publication: Research - peer-reviewJournal article – Annual report year: 2009

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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
Publication date2009
Issue27
Pages4666-4673
ISSN1434-193X
DOIs
StatePublished
CitationsWeb of Science® Times Cited: 19

Keywords

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