New strategy for the construction of a monotetrahydrofuran ring in annonaceous acetogenin based on a ruthenium ring-closing metathesis: Application to the synthesis of Solamin

G Prestat, C Baylon, M P Heck, G A Grasa, Steven Patrick Nolan, C Mioskowski

Research output: Contribution to journalArticlepeer-review

34 Citations (Scopus)

Abstract

An original convergent total synthesis of Solamin (type A annonaceous acetogenin) was achieved. The central THF core was obtained by means of a ring-closing metathesis (RCM) reaction using a ruthenium imidazolylidene complex. The RCM substrate was prepared from a vinyl-substituted epoxide by reaction with an allyl alcohol, both synthesized from propargylic alcohol. The flexibility of the strategy should be useful in preparing various natural and unnatural annonaceous acetogenins.

Original languageEnglish
Pages (from-to)5770-5773
Number of pages4
JournalThe Journal of Organic Chemistry
Volume69
Issue number17
DOIs
Publication statusPublished - 20 Aug 2004

Keywords

  • 1ST TOTAL-SYNTHESIS
  • OLEFIN METATHESIS
  • STEREOSELECTIVE-SYNTHESIS
  • STEREODIVERGENT SYNTHESIS
  • CYTOTOXIC ACETOGENIN
  • CONVERGENT SYNTHESIS
  • MODULAR SYNTHESIS
  • ORGANIC-SYNTHESIS
  • CIS-SOLAMIN
  • D-GLUCOSE

Fingerprint

Dive into the research topics of 'New strategy for the construction of a monotetrahydrofuran ring in annonaceous acetogenin based on a ruthenium ring-closing metathesis: Application to the synthesis of Solamin'. Together they form a unique fingerprint.

Cite this