Synthesis and assignment of absolute configuration of the Lridoid 9-deoxygelsemide

Alessandro D'Alfonso, Maurizio Pasi, Alessio Porta, Giuseppe Zanoni, Giovanni Vidari

Research output: Contribution to journalArticle

Abstract

[Chemical equation presented] The first enantioselective synthesis of 9-deoxygelsemide, belonging to a rare group of iridoids isolated from Gelsemium plants, Is described. The key synthetic steps are a variant of the Woodward-Prevost reaction to install the characteristic c/s-α-1,2- dioxygenated system at C-6 and C-7 with complete diastereoselectivity. Construction of the dihydropyran ring was achieved via formylation of lactone I, followed by dehydration of the corresponding lactol. The synthesis allowed assignment of absolute configuration to 9-deoxygelsemide and related irldoids.

Original languageEnglish
Pages (from-to)596-599
Number of pages4
JournalOrganic Letters
Volume12
Issue number3
DOIs
Publication statusPublished - Feb 5 2010

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

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    D'Alfonso, A., Pasi, M., Porta, A., Zanoni, G., & Vidari, G. (2010). Synthesis and assignment of absolute configuration of the Lridoid 9-deoxygelsemide. Organic Letters, 12(3), 596-599. https://doi.org/10.1021/ol902809v