Synthesis of Calystegine A(3) from Glucose by the Use of Ring-Closing Metathesis

Rune Nygaard Monrad, Charlotte Bressen Pipper, Robert Madsen

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Abstract

A synthesis of the nortropane alkaloid calystegine A(3) is described from D-glucose. The key step employs a zinc-mediated tandem reaction where a benzyl-protected methyl 6-iodo glucoside is fragmented to give an unsaturated aldehyde, which is then transformed into the corresponding benzylimine and allylated in the same pot. The functionalized nona-1,8-diene, thus obtained, is converted into the seven-membered carbon skeleton in calystegine A(3) by ring-closing olefin metathesis. Subsequent deoxygenation by the Barton-McCombie protocol, hydroboration and oxidative workup followed by hydrogenolysis affords calystegine A(3). The synthesis uses a total of 13 steps from glucose and confirms the absolute configuration of the natural product.
Original languageEnglish
JournalEuropean Journal of Organic Chemistry
Issue number20
Pages (from-to)3387-3395
ISSN1434-193X
DOIs
Publication statusPublished - 2009

Keywords

  • Natural products
  • Total synthesis
  • Metathesis
  • Carbohydrates
  • Allylation

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