Studies towards total synthesis of antillatoxin: Synthesis of C1-C11 fragment

Article abstract of DOI:10.1016/S0040-4039(97)10827-9

Synthesis of the key intermediate (5) of Antillatoxin (1) is presented. The synthesis is based on the indium-mediated allylation of 2,4,6,6-tetramethyl-2,4-heptadienal (3) and methyl (Z)-2-(bromomethyl)-2-butenoate (4) in saturated ammonium chloride catalyzed by lanthanide triflate which afforded the corresponding product 2 in good yield and high syn selectivity.