Enantioselective Syntheses of the Proposed Structures of Kopeolin and Kopeolone - Aix-Marseille Université Access content directly
Journal Articles Chemistry - A European Journal Year : 2013

Enantioselective Syntheses of the Proposed Structures of Kopeolin and Kopeolone

Stephanie Miquet
  • Function : Author
Nicolas Vanthuyne

Abstract

The first total syntheses of the proposed structures of kopeolin (1) and kopeolone (3) have been achieved from a common enantiopure chiral building block obtained by a chemoenzymatic enantioconvergent methodology. The syntheses feature two key steps: a one-pot reduction/ diastereoselective protonation followed by a highly diastereoselective addition of an organocerate. The synthetic structures were fully characterized and all stereocenters were confirmed. The results show that the two previously reported structures were not assigned correctly, and suggest an initial structural misassignment during the isolation of the natural products. Thus, two revised structures, 1' for kopeolin and 3' for kopeolone, are proposed.

Dates and versions

hal-01460462 , version 1 (07-02-2017)

Identifiers

Cite

Stephanie Miquet, Nicolas Vanthuyne, Paul Brémond, Gérard Audran. Enantioselective Syntheses of the Proposed Structures of Kopeolin and Kopeolone. Chemistry - A European Journal, 2013, 19 (32), pp.10632--10642. ⟨10.1002/chem.201300711⟩. ⟨hal-01460462⟩
133 View
0 Download

Altmetric

Share

Gmail Facebook X LinkedIn More