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 af...

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Bibliographic Details
Published inEuropean Journal of Organic Chemistry Vol. 2009; no. 27; pp. 4666 - 4673
Main Authors Dam, Johan Hygum, Madsen, Robert
Format Book Review Journal Article
LanguageEnglish
Published Weinheim WILEY‐VCH Verlag 01.09.2009
Wiley
Wiley-VCH
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Summary: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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) The antitumour agent pancratistatin is prepared in a total of 25 steps from piperonal and xylose. The key transformation is a zinc‐mediated tandem reaction between allylic bromide A and iodofuranoside B. Subsequent ring‐closing metathesis furnishes lactone C, which is then converted into the natural product.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200900719