Journal article
Convergent Synthesis of Pancratistatin from Piperonal and Xylose
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. (
Language: | English |
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Year: | 2009 |
Pages: | 4666-4673 |
ISSN: | 10990690 and 1434193x |
Types: | Journal article |
DOI: | 10.1002/ejoc.200900719 |
ORCIDs: | Madsen, Robert |