AI Article Synopsis

  • - The study presents the first asymmetric total synthesis of andranginine using an asymmetric Morita-Baylis-Hillman reaction followed by a diastereoselective intramolecular Diels-Alder reaction.
  • - Analysis of the natural andranginine extracted from Kopsia arborea shows it exists as a scalemic mixture.
  • - The predominant form found in the natural sample is identified as (16R,21S), rather than the (16S,21R) configuration.

Article Abstract

The first asymmetric total synthesis of andranginine (1) via an asymmetric Morita-Baylis-Hillman reaction and a diastereoselective intramolecular Diels-Alder reaction has revealed that natural andranginine (1) isolated from Kopsia arborea existed as a scalemic mixture and contained predominantly the (16R,21S) form rather than the (16S,21R) form.

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http://dx.doi.org/10.1021/acs.orglett.7b01076DOI Listing

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