New methodology for the synthesis of tetrahydrofuro[3,2-b]furan-2(3H)-one derivatives, synthons of natural products with biological interest

Ángel M. Montaña, Joan A. Barcia, Pedro M. Grima, Gabriele Kociok-Kohn

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

A new methodology is presented to synthesize in a regio and stereoselective manner tetrahydrofuro[3,2-b]furan-2(3H)-one, structural subunit present in a wide variety of natural products present in plant, fungi, algae, insects, and other living organisms. This secondary metabolites have important biological properties and have shown to be very active in different therapeutic areas. This method consists in the reaction of highly substituted 2-oxyallyl cations, generated in situ from the corresponding dihaloketone, and 2-functionalized furans (in our case 2-NHBoc-furan). It is a one-pot reaction that affords the desired furofuranones with high regio- and stereoselectivity. The new synthetic method is simple, straightforward and versatile, because a wide variety of furofuranones, and with wide molecular diversity, may be prepared by adequately designing the substituents of starting materials. The resulting furofuranones may be potentially derivatized to generate chemical libraries of high molecular diversity, which are very useful when developing structure–activity relationship studies.

Original languageEnglish
Pages (from-to)6794-6806
Number of pages13
JournalTetrahedron
Volume72
Issue number43
DOIs
Publication statusPublished - 27 Oct 2016

Keywords

  • 2,6-Dioxabicyclo[3.3.0]octan-3-one
  • 2-Functionalized furans
  • Furan
  • Haloketones
  • Oxyallyl cation
  • Tetrahydrofuro[3,2-b]furan-2(3H)-one
  • [3+2]-Cycloaddition
  • [4+3]-Cycloaddition
  • γ-Lactones

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