Synthesis and stereochemistry of β-aryl-β-haloacroleins: useful intermediates for the preparation of (Z) and (E)-2-en-4-ynecarbaldehydes and for the synthesis of rubrolides

Abstract

The synthesis of α-substituted β-aryl-β-haloacroleins by two different pathways is presented. The determination of their stereochemistry by NOE experiments is reported for the first time. Furthermore, we describe the preparation of 2-en-4-ynecarbaldehydes and access to rubrolide derivatives from β-aryl-β-haloacroleins.